Why is this man who is totally out of my league pursuing me?
April 30, 2015 11:43 AM   Subscribe

I dumped a guy who's totally out of my league. Now he is chasing me like there's no tomorrow. Why? And will it last?

I am a 30-year-old female who has been in only one real relationship and has had a bunch of terminal first and second dates aside from that. I was kind of a late bloomer and didn't even kiss a guy until I was 27. (Now you know why this post is "anonymous"!) My ex boyfriend at 27 was very sweet and devoted, but I didn't really respect him because I was smarter/more responsible than he was and felt more like his mother than an equal partner.

Two months ago, an interesting guy contacted me online. He was ten years older, but he was very polite and we seemed to have common intellectual interests, so I agreed to go out with him. Our first date was dinner at an expensive restaurant. He's very conventionally attractive and has a prestigious job and seems very self-assured, but frankly I wasn't sure we were a match. I'm kind of a shy, mousy person and I felt like his personality might be too strong for mine. He contacted me EVERY DAY since the first date, and I went out with him a second time - though I didn't feel a spark - and then I "dumped" him (as he put it).

After I turned down a third date, he seemed disappointed and immediately sent me a gift (it was an Amazon e-book that he thought I might enjoy). He requested that we stay in touch as friends and keep going to things together and "maybe you'll change your mind." I declined his offer to go to the theater together on his dime, because frankly it seemed like a date and I didn't want to mislead him... but then two weeks later I changed my mind and cautiously went on a third date with him. To my surprise, I ended up really liking him on our third date! I saw a more playful side of him, and I stopped being sort of creeped out by his intense interest in me.

Incidentally, he took his dating profile offline at some point after our first or second date. We haven't discussed this at all, but I noticed (when I decided to go on a third date with him) that his profile was gone! Mine is still up, but I stopped logging into the site after our third date. My friend checked for me recently--and his profile is still offline.

Long story short: We have now been dating for two months, and he is pursuing me VERY heavily, but I am racked with all these doubts about us. I don't really understand why he is so interested in me. He's very smart, very handsome, in perfect shape, has a great career, has tons more money than I do... keeps buying me presents ALL the time.... We haven't even done more than a quick kiss here or there in public! We haven't been to each other's apartments. What is he getting out of this? Frankly, I'm concerned that he might just be into me because I dumped him after two dates - but he actually started pursuing me pretty heavily since BEFORE we met. Taking someone out to dinner on a first online date is a bit much. It's almost like he made up his mind about us before he even met me. He contacts me every single day, asks me all these in-depth questions about my family and my childhood and my dreams for the future, buys me presents for no reason, even bought me a year-long membership to something....

My main concerns are:

1) Why is he so enamored with me when he's smarter, has more money, is objectively better than I am at all sports and lots of practical matters, etc.? Does he really enjoy the "teaching and caretaking" role, or will he inevitably lose respect for me? What do I bring to the table, besides my relative youth?

2) Will he lose interest as quickly as he developed it? "Blowtorch" phenomenon?

3) Will he eventually stop showering me with gifts and daily attention? This doesn't really seem sustainable.

4) To what extent is his hot pursuit fueled by the fact that I was reluctant at first? Physically, we haven't done more than a quick peck on a street corner. Will his interest dwindle away after he's "gotten" me? (He lived with his previous girlfriend so I know he's not waiting for marriage... LOL.)
posted by anonymous to Human Relations (64 answers total) 5 users marked this as a favorite
 
Why is he so enamored with me when he's smarter, has more money, is objectively better than I am at all sports and lots of practical matters, etc.?

A: Because these things do not determine what he likes about people.

Tip: try loving yourself a little bit more.
posted by entropone at 11:46 AM on April 30, 2015 [45 favorites]


Nobody can answer the questions you've asked here except him and/or time.
posted by trunk muffins at 11:50 AM on April 30, 2015 [4 favorites]


Ew, this question is throwing up all kinds of red flags for me with regard to him not respecting your boundaries and trying way WAY too hard to insinuate himself into your life. There's way more going on here than who is in who's league.

If you're this uncomfortable now, I say trust your gut and move on.
posted by vignettist at 11:50 AM on April 30, 2015 [59 favorites]


entropone beat me to it. The objective facts say that he's crazy about you, and this is how he shows it. If anything, he seems to think he's not good enough for you, and tries to make up for it with lots of presents and affection.
posted by Mogur at 11:51 AM on April 30, 2015 [4 favorites]


First and foremost, I see a heavy dose of you not giving yourself enough credit.

There are also some other, more cynical possibilities here that I'm sure other people will bring up.
posted by cnc at 11:51 AM on April 30, 2015 [1 favorite]


He sounds sweet and interested. Why end things before they've begun? If you keep dating him and realize that he creeps you out more than intrigues you, end things then. But so far he sounds like a man who is serious about finding a relationship and interested in you.

It's not fun to date with low self-esteem-- you end up with guys like your ex, who seem "safe" because you feel smarter and more mature than them. It's safer to be the catch and know it than to feel like you could lose the one you love. It's common for women who underestimate their attractiveness and charm to date down and become a mother figure in their relationships. But try taking a risk on love, if you really like this guy! It sounds like you could be equals.

There is definitely the possibility that he's a creep-- if he squicks you out, you have no obligation to keep dating him (and you should protect yourself). But it's definitely possible from what you've written that he just likes you and wants to share things with you (an ebook is actually a rather thoughtful gift, not as tacky as showering a woman with gold bracelets so she won't lose interest or something).
posted by easter queen at 11:53 AM on April 30, 2015 [17 favorites]


I would suggest you really look at the rules for how relationships progress that you have created in your head. He could be a really decent kind man who enjoys your company but your low self esteem is going to get in the way of being able to accept and enjoy this kind of attention.
posted by cairnoflore at 11:54 AM on April 30, 2015 [4 favorites]


Because he perceives you as having low self-esteem, which makes you easy to dominate, exploit, and abuse, which is what he's going to do if you fall for his bullshit. Respect yourself more and move on.
posted by matildaben at 11:55 AM on April 30, 2015 [36 favorites]


I think if it feels weird, it's weird. You're allowed to break up with this guy if things don't feel right. If the only problem you're worried about is what will happen if the other shoe drops, I think you can rest in the knowledge that it will, and just wait for that to happen.
posted by ThePinkSuperhero at 11:55 AM on April 30, 2015 [9 favorites]


Life experience tells me he will completely go fickle of you once you return his passion for you - he just likes the challenge you are presenting.

The romantic in me says this might be the real deal.

I don't know!! I don't think there is any way to tell. Hmmmm. Do you like him? Do you feel a spark?

I imagine this is difficult if you are holding back emotionally. I'm also pretty sure you are not giving yourself enough credit, that's certain. Hmmm. Hard to say! I guess you're just going to have to wait it out, or hire a private detective or something. I have no idea. Really.

Anyway, if you like him, date him. If you do not like him, stop dating him and don't accept anymore gifts.

The gifts make me leary. He could be mentally ill or something. Or maybe just a really great guy ready to settle down! Arghhhh! I don't know!!

What do you think is going on?
posted by jbenben at 11:55 AM on April 30, 2015 [5 favorites]


A few thoughts:

1) People are allowed to find you awesome. How we relate to other people isn't a 1:1 competition. You clearly have qualities that he values and he clearly finds you interesting. You sound very negative about yourself, which is too bad.

2) This guy's level of attention would annoy the hell out of me. I would feel completely smothered and it would ring personal alarm bells for my level of comfort in a partnership. If your brain is telling you there's something wrong with the situation, listen to it.

3) Instead of focusing on the ways that you think he's better than you, or why/if he likes you, focus on the things you like about him. Focus on the qualities he has that would make him a good match for you. A lot of times in early dating, folks fret over what the other person thinks about them, to the exclusion of even feeling out the relationship to see if it's a good fit. Don't lose sight of that.
posted by phunniemee at 11:56 AM on April 30, 2015 [30 favorites]


A couple of possibilities here:

1) he's a cool guy and thought there was a real spark between the two of you and doesn't want to give up on you yet
2) he's a boundaries-pushing creep who won't take no for an answer

Whether he's "out of your league" or not has nothing to do with it.
posted by mskyle at 11:56 AM on April 30, 2015 [70 favorites]


Dude really likes you. Do you really like him too, for more than his descriptors? And beyond being interested in you, is he respectful of you and attentive to your boundaries? If you like him for himself and he is respectful, I'd suggest talking to him about your concerns about how intensely focused on you he seems to be.

My husband fell for me right away. I really lacked faith in my own judgment at that point and it all felt too fast to me. But I was able to talk to him about that. The ability to safely and trustfully talk to a partner is a real indicator that what is happening is for real .
posted by bearwife at 12:00 PM on April 30, 2015 [10 favorites]


I just noticed this "but then two weeks later I changed my mind and cautiously went on a third date with him". Did he give you that two weeks without bugging you? Or was there a continual bombardment until you gave in? If the former, great! If the latter, alarm!
posted by Mogur at 12:02 PM on April 30, 2015 [13 favorites]


I suspect you are not giving yourself enough credit. However, that does not mean this is the guy for you. For what it's worth, here are the red flags I see:

After I turned down a third date, he seemed disappointed and immediately sent me a gift (it was an Amazon e-book that he thought I might enjoy).

Pushing your boundaries by taking advantage of the norms of reciprocity. Charities apply the same technique when they mail you "free" address labels.

It's almost like he made up his mind about us before he even met me.

Typecasting. It may be that he's less in love with the real you and more in love with the version of you he expects you to be. This is dangerous because in the future, he will hold you to his version of you. It also may be that he's more interested in the version of you in his brain than in getting to know the real you.

He contacts me every single day, asks me all these in-depth questions about my family and my childhood and my dreams for the future, buys me presents for no reason, even bought me a year-long membership to something...

Pushing the timetable. And potentially ignoring your boundaries and preferences in the process.

I dunno. Does he have positive relationships with the women in his life, including exes? Does he ever talk to you about how you're "not like that bitch !ExName"? If so, run now.
posted by pie ninja at 12:03 PM on April 30, 2015 [28 favorites]


Will he eventually stop showering me with gifts and daily attention? This doesn't really seem sustainable.

That's going to happen. No relationship stays in a courting/infatuation mode forever.

I can't answer any of your other questions, but you seem really down on yourself. You might be right in thinking that the initial rejection was what attracted him or that he'll quickly lose interest at some point (both are things that really happen sometimes), but you don't seem to accept even the possibility that he could just find you really attractive. Whatever you do with him (lots of thoughts on that above), I think you should work on that.
posted by Area Man at 12:07 PM on April 30, 2015 [1 favorite]


I cannot answer your questions.

But I have some homework for you that will help you answer them.

First, Ask him some questions. Where are his exes now? Find out about his female friends and colleagues. Does he buy these types of gifts for men, ever? A brother? A close college buddy? If yes it's less red flaggy.

Second, read some books. I'd suggest three:

The Five Love Languages, because this could be as simple as you not really being into gifts or words of affirmation and that's why this is weird for you. But it could be actually creepy. Either way, it's good to know about your own love language and helpful to be able to identify them in others.

Brene Brown's The Gifts of Imperfection, which I hope will give you some space to accept all of your beautiful quirks.

What Makes Love Last by John Gottman and Nan Silver. This will help you lay the groundwork for future relationships.

And since I suggest this video all the time, Sliding Vs. Deciding, which is an hour long lecture about the importance of making choices rather than just falling into relationships. This guy might be trying to slide you into a relationship. But maybe not. Either way, it's good to be wary of sliding, and to focus on commitment to things that are important to you, both inside and outside of romance.
posted by bilabial at 12:18 PM on April 30, 2015 [10 favorites]


You know who can answer your questions? He can. Ask him.
posted by Leontine at 12:19 PM on April 30, 2015 [6 favorites]


I think his ego is bruised and he wants to get back together so he can be the one to dump you this time. He's clearly not respectful of boundaries. Dude's not as good as he seems.
posted by Hermione Granger at 12:25 PM on April 30, 2015 [3 favorites]


Maybe he's not that into ranking people by which "league" they are in and whether they are "worthy" of various other people.

Do you like him? Find out if you like him.
posted by amtho at 12:31 PM on April 30, 2015 [4 favorites]


I think you should ask him. But I also think you should meet his friends and get a feel for what kind of person he is from them. As an aside, my partner fell in love with me way before I fell in love with him. But I decided to just explore what might happen if we kept dating because he seemed sane, smart and sexy and so why not? He turned out to be the real deal. He is awesome. But as MeFites know, there are many abusers out there as well as folks who are simply poor matches. He may, in fact, just have a different love language than you. You may, in fact, be far more awesome than you give yourself credit for. It may be that you are an especially good match for him. But that doesn't mean he's necessarily a good match for you. How can you find out? Keep dating him. And talk to him. And to his friends. And his family. If he has no friends or family, that's a really good reason to break up now. Because that is a huge red flag. But if your main problem is that he's treating you too well, keep seeing him and see how things shake out. Why not?
posted by Bella Donna at 12:31 PM on April 30, 2015 [6 favorites]


"I think his ego is bruised and he wants to get back together so he can be the one to dump you this time."

I actually had someone do that to me once. Before it happened, I didn't know people could be like that. They guy who did it was close to your guy's profile - older, attractive, successful. He'd never been married, but had at least one serious ex girlfriend. He didn't shower me with gifts, though, so at least that was different.

Don't know if that info helps you. But there ya go.
posted by jbenben at 12:34 PM on April 30, 2015 [3 favorites]


It's almost like he made up his mind about us before he even met me. He contacts me every single day, asks me all these in-depth questions about my family and my childhood and my dreams for the future, buys me presents for no reason, even bought me a year-long membership to something....

These are red flags to me, personally. It's too much, too intense, too fast, too seemingly-intentionally-overwhelming. Take a look into lovebombing and see if it rings any bells -- or at least gives you more to keep an eye out for. Set some boundaries (e.g., "I'm going to be really busy with family/work for the next two days, can we put texting on hold until Thursday?" or "I'm not comfortable receiving this many presents") and pay attention to how well he respects them. How focused is he on continuing his current course and speed (the pace/intensity that HE has set between you, not a mutual one) vs. ensuring that you are comfortable and happy? Are there signs that he thinks he knows better what's right for you two, compared to what you say/feel?

This has nothing to do with whether you're totally desirable as you are or any accounting of "leagues," by the way. If he really is simply smitten with you (and why not!), he will bend over backwards to make sure you feel comfortable and happy. He will be delighted that you tell him how. Anything else is worth keeping your spidey-sense tuned to. I think you have great instincts, and I'm glad you're having fun. Be confident that you have 100% as much say as how things go between you do as he does, and if it doesn't feel good or right, that matters much more than any of his attributes 'on paper.'
posted by argonauta at 12:35 PM on April 30, 2015 [8 favorites]


I'm concerned that you're the female version of the stereotypical "bad boy" that many a woman love to date...aloof, hard-to-get, unavailable, a mystery and an enigma all wrapped into one. You might simply represent an extraordinary challenge for him. It's exciting. That doesn't necessarily mean you are sport to him, but I would be concerned.
posted by teg4rvn at 12:37 PM on April 30, 2015 [5 favorites]


You're setting yourself up for a one up/one down kind of situation here, rather than a partnership between two equals, and that just isn't healthy. Does this guy ever - EVER - give you reason to believe he agrees with your assessment of the situation? Because even a whiff of him agreeing that he's in the superior position here or is somehow being "generous" in seeing you wouldn't just be a red flag for me, it would need to be the end of the game.

Even if he doesn't seem to share your view, I strongly agree with the people saying that you need to work on reassessing this situation in your head - he may be in a different place than you in life but there really is no such thing as a "league," and you guys are perfectly capable of being equals who bring different but equally valid things to the table. Beyond that, I think you might want to shift your focus to different questions than the ones you've laid out here - less about "why is he doing what he's doing and what's he going to do next?" and more about "How do I feel about him and what he's doing, and what do I want to do about it?"

Personally, I would feel really put off and smothered by someone who came at me so soon with such intensity - I've "dumped" potential friends before for exactly this reason. The fact that you're inexperienced at dating makes this seem like a situation to be particularly cautious of. At the very least - if you feel like you could be interested in him and want to see how things go - I would suggest you figure out what you are and aren't comfortable with and then communicate that to him. If he respects your boundaries, great; if not, you'll know you're with someone who isn't so great to be with, after all.
posted by DingoMutt at 12:43 PM on April 30, 2015 [6 favorites]


Being "out of your league" is not the issue here. (If anything, he seems to have put you on a bit of a pedestal, and might well think you're out of his league.)

But what I see in your post is that he was coming on very, very strong, which made you uncomfortable, at least at first. And I think you should listen to your gut, and ask yourself, does the intensity of his courtship still make you uncomfortable? Trust your gut!

If the answer is yes, and you still want to see him, it is totally okay to ask him to dial it down a little. Something like the following is a totally reasonable request: "Hi, I would like to keep seeing you, but frankly, the fact that you are giving me so many presents is making me a little bit uncomfortable. Could you maybe stop buying me things for now?". The way he replies I think is also an indication of his intentions and character; if he tries to argue back, or make you feel bad for making the request, that's a giant red flag.
posted by water under the bridge at 12:50 PM on April 30, 2015 [4 favorites]


I had something like this, where I almost missed out on my wife's romantic pursuit of me because I always thought she was "out of my league," and thus thought she was just a really good friend. In hindsight, man, what a dumbass thing--we're matched pretty evenly in every way. Especially now that we've spent a decade growing together.

Part of your feeling unmatched with him might be the age difference--where he's at in life, career, etc., are different or "better" than you simply because he's been at it a decade longer than you. Look at it this way: was he about where you are now ten years ago when he was 30? Would 30-year-old him be out of your league? As to looks, you don't say that you're mortifyingly hideous, so who's to say you're not darned good looking? This guy sure seems to think so... Forget about athletic abilities and stuff like that--it's normal not to try to marry a hiking or dive buddy or squash partner if he already has those. Watch out if he tries too hard to make you into those things....

At 30 you're probably "too old" to be a "project" for him to "mold" if he's one of those control freaks; if he's as handsome and kind and well-off as you suggest, he could easily have picked up some undergrad by now.

You have "intellectual interests," you like to read, you are a concise, clear writer, you laid the problem out for us showing that you've thought through all the possible issues even though you have relatively little dating experience...all of which is to say, you might be awesome. I second those above who suggest you might be undervaluing yourself. If this guy is going all-in for you--this guy who looks great on paper and seems to check off all the conventional boxes of potential good boyfriend, and presumably would know a good deal when he sees it--then you might just be undervaluing yourself.

As to wanting to know a lot about you....some dudes are just like that. It can be creepy, but it can also be endearing. If he's head over heels smitten, it makes a lot of sense to want to know your story and how come you're you.

As others have noted, if you're comfortable with the boundaries he's pushing, and you really like him otherwise, then keep going on in one another's company--what's the worst that could happen? You break up?
posted by resurrexit at 12:51 PM on April 30, 2015 [1 favorite]


1) Why is he so enamored with me when he's smarter, has more money, is objectively better than I am at all sports and lots of practical matters, etc.? Does he really enjoy the "teaching and caretaking" role, or will he inevitably lose respect for me? What do I bring to the table, besides my relative youth?

He isn't comparing you to HIMSELF. He is comparing you to OTHER WOMEN.

You say you are smart. Smart people often have trouble finding someone who is their intellectual equal, but most people marry someone who is within 10 points of their IQ.

You told him "no" even though you are younger. I bet a lot of women meet him, see he is good looking and has money and throw themselves at him in hopes of getting what you are getting: showered with prezzies. You don't care about his money. That is likely to make you one of the most attractive women he knows.

If he is that successful, he is probably an aggressive go-getter. He doesn't wait for things to happen. He makes things happen. So, yeah, he is going to be like that in all things, even romance.

If he has a lot more money than you, what he is spending on you doesn't hurt his wallet as much as it impresses you. Don't worry about it.

Enjoy what he gives you. Keep telling him "no" when you feel that is the correct answer. Let him know if you want him to back off a bit.

When someone is pursuing you this hard, you are the person in the position of power. He has to meet your demands if he wants you. So play to your position of strength. Insist he do things your way on matters that really matter to you. And then que sera sera. Him being this enamored now doesn't mean the relationship will last. Let it play out how it is going to play out. Just make sure you keep telling him what you need to tell him to set appropriate boundaries and keep a life of your own.

The fact that you are not willing to be a bauble on his arm and you do have a brain of your own and ideas of your own is your most attractive feature. Make sure you keep those things and you will be okay whether this leads to marriage or is just a funny story a few years down the road.
posted by Michele in California at 12:56 PM on April 30, 2015 [13 favorites]


You've gotten good advice above and I think it's all worth considering. Trust your instincts. I just want to add that all types of people (age, gender, experience, physical attributes, social/class status, responsibility level, etc) can potentially find all other types of people attractive and desirable. There's no rule that conventionally attractive and fit people must be interested in other conventionally attractive and fit people, for instance.
posted by dchrssyr at 1:39 PM on April 30, 2015 [2 favorites]


His intense pursuit makes me wonder if he's a little socially inept. If you're looking for a reason why he's not already with someone you consider higher status, that could be it. He also might be really wanting to be in a relationship/ have a family ASAP and is throwing all this energy in that direction.
posted by metasarah at 1:43 PM on April 30, 2015


I will also suggest that instead of viewing him as "better" or "more established" than you, it might help to view him as being from a different world. Assume you fundamentally don't understand what his life is like. Pretend he is simply from another culture and grew up speaking a different language from you.

Instead of being intimidated, cultivate an attitude of dispassionate intrigue. "Oh, that's fascinating. I would have never done it that way. I wonder why he does it that way? I mean, to me that means (blah and yadda). I can't imagine why else he would do it that way. But, surely, he has some good reason for doing the things he does (since blah and yadda are probably both negative and also wrong). I wonder what the backstory is. I wonder what that means in context from his perspective."

He's still a human being with human needs, never mind his money and what not. Try to figure out how to interact with him like a human being. Assume you don't know what his motives are. Do not assume they are nefarious. If they are nefarious, you will eventually find that out. But just focus on finding out what motivates him and leave judging those motives until you actually know what they are.
posted by Michele in California at 1:55 PM on April 30, 2015 [2 favorites]


Maybe he's actually a creepy abuser, but maybe he's just a generous guy who's falling for you fast. I'd talk to him about where you are and the boundaries you want right now - fewer or no presents? Less frequent contact?

As I've gotten older, I tend to get into serious relationships faster because I recognize what's going to work faster. But it's important to tone down the intensity and pacing to where your partner is. If you tell him to slow down and give him limits and he doesn't respect those, it's a very, very bad sign.

You may also want to turn the spotlight on him a little. What's he looking for in a relationship? Is he on the rebound from a very recent divorce? What are his dreams and goals? How does he feel about his life?

You will need to be able to meet him on equal footing for this to work, and getting to know him well enough that he doesn't feel "out of your league" is important. I've definitely felt like that when I've started dating people, and had it shift into "they're the most amazing magical special best person in the whole world" to "I love this unique and ordinary and perfect and broken human more than I can bear." It helps to recognize your own value here.
posted by congen at 2:02 PM on April 30, 2015 [1 favorite]


This sounds really fishy as you've described it and if it was happening to me, I'd be suspicious too (no, I have no problems with my self esteem).

I'd trust yourself and move on. He's way too pushy to not be up to something.
posted by longdaysjourney at 2:22 PM on April 30, 2015 [4 favorites]


Primates measure their mates by their social dominance. Rejecting someone is a demonstration of social dominance. Hence, you are measured highly.

In other words, people want what they can't have.

Also, THERE ARE NO LEAGUES repeat it 1000 times over.
posted by Ironmouth at 3:09 PM on April 30, 2015


This guy's behavior is a little weird. He's not out of your league. There are no leagues.

Why is he acting weird? I have no idea. He could be a great guy, and he could be a creep. But his behavior is a bit strange, at the very least.
posted by breakin' the law at 3:20 PM on April 30, 2015 [1 favorite]


You are probably awesome, but you are probably the youngest woman to take an interest in him and he has learned that women in their early-mid 20s don't always want to immediately pair up with a guy approaching his 40s like a lot of guys think they will if they're wealthy and in shape.

He sounds weird with the present giving, etc, change your mind hope, etc. It's weird, he barely knows you, and he seems fixated on you. Red flags, not sweet.
posted by discopolo at 3:21 PM on April 30, 2015 [1 favorite]


The observation that other commenters have made about you loving yourself more is golden. Regardless of this guy's motivation for pursuing you, self-confidence is one of the most attractive qualities an individual has.

That said, acknowledging reality is also important. Conventional laws of attraction are exactly that: convention, although there are exceptions to the rule, which is when we might think to ourselves, "Wow, why is that gorgeous woman with that dumpy little fella?" Obviously, the questions you've asked will only be answered by time. I won't presume to think that this guy's intentions are good or bad, nor do I think his overwhelming pursuit of you is a red flag, but here's my anecdata that may give you insight.

For the longest time, I dated guys that would've considered themselves way out of my league, and those relationships spiraled down the drain eventually. My friends would wonder why I did, and I'd tell them the guy was smart, had a great personality, etc., all of which were true. The thing is, I'd always be the one to dump them... until someone dumped me first. I was out of his league, he'd acknowledged that, but apparently our incompatibilities were significant enough for him that me being a 'catch' didn't outweigh our differences. Boy, did I hate him for it. It took me a long time to get over that guy, and deep down I realized it wasn't that I actually thought he was the love of my life or "the one". He just basically busted my ego. And my reaction to being dumped sent me into therapy, where I realized that subconsciously I'd date people who weren't "conventionally attractive" because I needed control.

C-O-N-T-R-O-L.

Don't get me wrong - I'm not superficial in that I ever believed someone was 'beneath' me, either intellectually or physically. There were genuine reasons why I was attracted to men that many women wouldn't consider conventionally attractive, but a small part of that was likely a need to control - with my looks, with their own acknowledgment that I was not someone they'd have considered pursuing because I'm out of their league. Does this make me a horrible person? No. But it did help me explore my need for control and helped me realize that sometimes, an even playing field is important when it comes to dating. If they're not, insecurities can set in that destroy the relationship.

This guy's actions are vaguely reminiscent of my own during that phase of dating. He seems to crave control. For now, you're not allowing him that control, so you're a challenge - but the way he's pursuing you looks like he's trying to control you. In no way does this mean you're somehow 'less' than him. You gave in to his relentless requests for a third date, and thus his need for control was temporarily satiated.

I hope I'm wrong, and that yours is a wonderful love story with a happily-ever-after. But, proceed with caution. Older men have baggage - they're single for a reason. His actions aren't normal for today's dating culture. Follow your instincts - you seem to have good ones - in protecting your heart and in putting your needs, boundaries and wants first.
posted by Everydayville at 3:23 PM on April 30, 2015 [11 favorites]


Maybe he's bad news, for the excellent reasons given by others above me. Maybe he's great, but for all his outward success, he's really insecure and trying way too hard to prove himself. Or something else. I don't know, but I for one have two questions:

- You said you dumped him, "as he put it." It strikes me that there must be a key conversation hidden behind those 4 words.

- You say you've been dating for two months, but also repeatedly that he's "pursuing" you and hasn't "gotten" you yet. What do these terms mean to you? What do you consider your status to actually be, and do you think he'd say the same thing?
posted by jinjo at 3:26 PM on April 30, 2015 [7 favorites]


"Out of your league? Son. Let women figure out why they won't screw you, don't do it for them." Change the genders as necessary and substitute "date" for "screw," and it's still sound advice. Don't take yourself out of the race before it starts.

Cross out the "out of my league" stuff, though, and your question becomes "Why does this guy continue to pursue me after I said no?" That's the question you should be more concerned with. Maybe he's deliberately pushing boundaries, maybe he's socially inept, who knows. Either way, outside of romantic comedies the inability to accept "no" for an answer is one of the biggest, reddest, wavingest red flags out there.

You like him now, and I don't really blame you, but your gut's telling you something isn't right. And it's not because he's handsome and smart and successful. It's because he's doing this weird fast-forwarding coming-on-too-strong thing. Most of the time, that ends up in a confusingly short-lived failed relationship. Sometimes it ends up worse. Listen to your gut. Trust the part of you that says "no." Proceed with caution.

Don't be afraid to say no to him (or anyone else) in the future. If you ever are afraid to say no, that's a sure sign that you should.
posted by Metroid Baby at 3:27 PM on April 30, 2015 [9 favorites]


How much time is he investing? Have you met his friends? I imagine players would give up after 20 hours tops, and wouldn't introduce you to friends.

What does his relationship history look like? Fewer relationships is more trustworthy but one sounds low. What was he doing for the last 20 years?

If he's investing insane amounts of time and social capital (money doesn't count) and has only recently gotten over whatever was limiting him in the past, then you're good to go. I can't predict long term success over text though.
posted by sninctown at 5:02 PM on April 30, 2015


That's an awful long time for adults to be dating without anything more than casual public kisses. Are you interested in sex? He might not be...
posted by Scram at 5:25 PM on April 30, 2015 [1 favorite]


So, I'm getting some weird vibes about boundary-pushing.

But I'm also getting a lot of vibes that you don't value yourself and that you and he come from different worlds. I mean, this guy is a 40 year old, successful man. The price of dinner, or a book, or theater tickets, is literally nothing to him. These are things he probably does with his friends and co-workers after work because, hey, you have to eat and have entertainment, so why not have dinner or catch a show? And the older you get, the more valuable time is, so why not do things you like while on a date?

I really think this could go either way. If you don't feel comfortable with him, trust your gut, I guess. But it's just hard to say with this information here. Maybe he came on strong because you're awesome and he likes you. Maybe he came on strong because he's recently divorced, or separated, or feels his biological clock ticking. Or maybe he's a creeper.

There's no way to know if he will lose interest you and cool off his pursuit. But I think that's the wrong question. The better question is whether he is a controlling creeper. Another better question is whether you like him. Him losing interest down the line as a possibility is of virtually zero consequence here -- if so, so what?
posted by J. Wilson at 6:09 PM on April 30, 2015 [2 favorites]


Lots of red flags here and I'm surprised by all the responses saying "he's just really into you!" He barely know you and you barely know him. It's way too early for such intense, all-consuming interest. This kind of boundary-pushing behavior early on in a relationship is a hallmark of men who later turn out to be abusive. He wants to reel you in so that he can start controlling you.

You are feeling uneasy for good reason. Trust your gut and call the whole thing off.
posted by RubyScarlet at 6:33 PM on April 30, 2015 [7 favorites]


I don't think the difference between 30 and 40 is really that big, especially when it's a 30-year-old woman and a 40-year-old man (I think now, at least in my experience, women in their late 20s/early 30s are much more mature than most men their age). So I don't really see that as the issue here. I don't see him pursuing you as an issue (although a little odd -- but I have also known men who do that with the best of intentions). If he can afford the gifts, I don't think that's a big deal either, on its own. Some people are like that.

What I do find weird is that you haven't been to each other's homes after two months and you haven't done more than kiss. Why haven't you been to his place? Why hasn't he been to yours? This feels like "he's hiding something."

I just feel like there's something else going on here he's not telling you about. Yes, you need to go beyond the "he's out of my league" thing and also have more confidence in yourself, but those are separate issues from what I think is actually going on here. But I don't know what's actually going on here. From my read, though, it doesn't seem good.
posted by darksong at 6:43 PM on April 30, 2015 [4 favorites]


In general I'm really pro-self esteem but I think it's weird when people say there are no leagues. Of course there are, and it's disingenuous to act like there aren't. I don't know you and I doubt that you're mousy, but I do trust your opinion that this guy is out of your league. That doesn't mean it can't work, or that his interest isn't genuine! It just adds another layer to the issue here, because if YOU were out of HIS league, I bet you'd think this was way creepier. Since he's older, richer, and better looking it's easier to give him a pass on his behavior.

I'm fat, so lots of people are out of my league. When I have dated/slept with dudes who were extremely conventionally attractive, it has been because they saw me as a fetish. In your case, it could be your youth, inexperience, and possibly that "mousiness" that is making him pursue you so hard, especially since you "dumped" him.

He could just really like you, but based on what you've said here, this guy sounds creepy to me. I would be very wary.
posted by masquesoporfavor at 7:17 PM on April 30, 2015 [1 favorite]


It's cliche, but time will tell.

I do agree maybe you need to give yourself a little more credit just as a general rule. You sound like someone lots of guys would be interested in but since you were a "late bloomer" you have some hangups about your desirability. I definitely am a more reserved person, and would describe my past self as mousy, and I used to be floored when random men would hit on me -- men who seemed attractive, put-together and outgoing. It was hard for me to accept that maybe I was attractive to these guys. I have also observed really outgoing people enjoying to spend time with people who are a little quieter that let lead the conversation a bit more.

With that said, sure, there are cynical possibilities. If this turns into a 50 Shades of Grey situation (I don't know, never seen the movie or read the books) where this dude is grooming you for his weird sex fantasies because he thinks your mousiness makes you a good mark, or if this guy becomes controlling, then that puts his aggressive pursuit of you in different light. We can't know if he's going to do that until he does. Could he be pursuing you for sport and he will lose interest once he wins you over or has sex with you? Maybe, but then you'd dodge a bullet because he would have major baggage if that were the case. Just try to keep an objective view of what's going on and look for any red flags. I'm sure if you're ever unsure, we will help you.

But still, I would add that some men are willing to put their heart on their sleeve and be very up front about their interest, and some people are intense. I have a friend who dated a man who was madly in love with her and was interested in her instantly, and always got her gifts, brought her flowers etc. He was just an intense guy, and she initially found him very romantic, but in the end, he was way too into her, to the point that it was a little embarrassing for her when they would go out together and he would get up and kiss her in between courses at dinner. He didn't turn out to be sociopath or anything, although he took being dumped poorly because she basically shattered his heart. I think they went out for a couple years, even though I think her friends found him a little intense.
posted by AppleTurnover at 7:39 PM on April 30, 2015 [4 favorites]


I've been dating my boyfriend for almost exactly one year. Yesterday I came home and he'd put flowers in every room of my apartment. One bouquet in the living room, one in the bedroom, and one in the bathroom. They were my favorite flowers and in all colors.

He's gotten me flowers every month or so since we started dating.

We probably seemed "boundary-pushing fast" to some people in the early stages of our relationship.

When we first started dating he had a much nicer apartment and car (and job) and more money than I did. As a result he was very okay with paying for things, although I honestly and sincerely tried to hold my own- and now we usually go dutch. (I make more now than I did then) But he's not 10 years old than me. He's five months younger.

So perhaps I'm biased, but most of this stuff sounds like pretty innocuous, traditional male courtship to me.

I need more signs of genuine creepiness or weirdness before I just write this guy off. Spending money on you, asking you for a date, buying you gifts- these are things men have done since the dawn of time. I don't really find that creepy at all, perhaps just unusual these days in certain blase hipster make-out-with-your-friend-and-don't-call-it-dating culture. Traditional, yes, but evil? (Well, to some they are synonymous...)
posted by quincunx at 7:44 PM on April 30, 2015 [3 favorites]


He contacted me EVERY DAY since the first date, and I went out with him a second time - though I didn't feel a spark - and then I "dumped" him (as he put it).... It's almost like he made up his mind about us before he even met me.

This would give me pause. Together with everything else, I'm getting a picture of a guy who's used to getting what he wants, and you're the thing he wants right now. It all feels a little too conquesty for comfort (to me, at least).

Full disclosure, I'm thinking through power stuff myself right now, conclusions TBD. But in case it helps at all, I do want to share with you the things that need to be happening in order for me to pass GO ("GO" probably means something different to me, but I think the following still applies) : I feel comfortable with the person, really quickly. Conversation is natural and unforced, and it's characterized by good timing - there's an easy back-and-forth, no weird pauses or talking over each other. There's a lot of smiling and laughing, on both sides. I feel centred. I'm not self-conscious, or acting like anyone other than myself. I notice we're both automatically physically leaning into each other. I want to be around him, because it feels good to be around him.

Whenever I've felt the above, things have gone swimmingly. Whenever I've felt nervous, or off-centre/on edge, or like I've had to think of things to say, or I've been aware that the other person was leading a lot, and that I've been working hard to respond (or to sound impressive, yikes), and especially when I've felt the angsty kind of butterflies, things haven't. If you're wracked with doubt, that's not ideal, imo.

I felt like his personality might be too strong for mine.

This is worrisome, imo.
posted by cotton dress sock at 8:20 PM on April 30, 2015 [6 favorites]


I agree with trunk muffins "no one can answer the questions except him and time." My caveat on that is that only you need your questions answered. First, ask yourself "Am I interested in this person?" You've already said you have been from the third date.

However I see from your description that you are not familiar with intimacy and an intimate relationship. I recommend this:

" Arthur Aron, a psychologist at the State University of New York at Stony Brook, is interested in how people form romantic relationships, and he’s come up with an ingenious way of taking men and women who have never met before and making them feel close to one another. Given that he has just an hour or so to create the intimacy levels that typically take week, months, or years to form, he accelerated the getting-to-know-you process through a set of thirty-six questions crafted to take the participants rapidly from level one in McAdams’s system to level two. The questions are part of an hour-long “sharing game” in which each member of a pair reads a question out loud and then they both answer it before moving on to the next question."

That came to me from a blog post I get emailed to me. I am not posting any of the sample questions that were in that blog post. You want them You'll find them. One thing that is very cool about it is the equal questioning and read to your partner. I haven't done this yet but I am dating someone new and looking forward to this getting to know you tool. Aron’s book is Handbook of Closeness and Intimacy.

After writing the above I read all the preceding answers. During that I recalled that you described being in a mothering position to your former boyfriend. Do you now feel the tables are turned? It came to me that perhaps that strong character, leader aspect is observable by him in you. Perhaps he actually finds you attractive because of what you are aware of in your last relationship, a characteristic of your self that you don't know you project - a strength in your personality a strength that is not an affect of your past relationship. In any case that quality will protect you from being dominated if the doubters prove to be right.

Surrender is what love is about. Not submission. You I suspect have never surrendered. Men are culturally required to pursue and women to choose. But both surrender to the other in love. Prepare yourself for the gift and the danger of that. What I suggest now may seem like woo but it's not. Many speak of boundaries. When it becomes confusing and you are unsure of what he is doing and wants and what you want and need to do, take a moment (preferably in private before you are with him) and visualize the interaction. At that moment feel your body, your sense of being in your body. Be aware of it being grounded through your feet or your bottom if sitting. Breath deeply and slowly and draw an arc with your foot in front of you and say softly to yourself "This is my boundary and you cannot come in unless I let you in". You can do this in public if feeling overwhelmed but do so surreptitiously with nothing more than inaudible whisper. It works.

You are smart enough to know what this man's intentions and level of respect are. You will recognize it. For an amazing story of a man wooing a woman (the good woo) rent the movie "The piano". Do not watch it with him unless you want to take the relationship to the next league errr level.
posted by Jim_Jam at 8:50 PM on April 30, 2015 [4 favorites]


I agree with everyone saying that you need to learn to love and value yourself more. I also think part of that is trusting yourself. The stuff about you not being good enough for this guy because he's out of your league is crap. The feeling of unease you have about this guy coming on way strong and giving you a lot of expensive gifts that will bind you to him? Yikes. I am saying this not just as a stripper where this behavior is rampant; as a uni student and in the normal world workforce, men who are pushy about not allowing you to break up with them and shower the objects of their romantic interest with expensive, obligation-making gifts are controlling and bad news. Complaining that someone you've been on two dates with "dumped you" is super possessive and SUPER BAD NEWS. Tread carefully. Find yourself a smart hot guy who isn't using guilt and manipulation tactics like "you dumped me" TWO DATES IN and who isn't trying to buy you.
posted by moonlight on vermont at 9:06 PM on April 30, 2015 [4 favorites]


He was ten years older

Is this not reason enough? How does that not put him "in your league"? 40 is getting to the age when people are really starting to think they need to be settling down soon. Barring a previous long term relationship or divorce, people might reasonably wonder why he's on the market at 40. Not saying they should, but people do think that way. He may correspondingly be in a rush to seal a deal, especially if he wanted kids.

Pardon me for being cynical, but if the genders and ages were swapped, wouldn't people find it odd, or at least that the older woman was "in the same league"? I'm not saying it would have to be odd, and I know a lot of people think a 10-year age gap isn't a big deal, but, frankly, it is. The seven years between my younger brother and I are enough for him to not remember a world before cell phones and the internet were ubiquitous, so we happen to see the world somewhat differently.

I have more stories from couples with ~10 year age gaps who didn't make it than couples who did.

Oh, and there's the bit where women are taught to devalue themselves (my girlfriend will admit to having been raised this way, and yes, she's on Metafilter. Hi!), another reason you might not think he's in your league when in fact, he is.

And yeah, I know it's common for younger women to prefer older men, because older men have a tendency to be wealthier, "more mature", more experienced, etc. This can be infuriating for men who want to date women who are their age. And for younger men who want fair consideration but can't expect it because the default preference is older men. Default preferences set up an in/out of league consideration for reasons that, in isolation, are kind of nutty, like preferring taller people.

I'll just echo what everybody else is saying, again: Respect yourself. Trust your instincts. I'll also point it out in slightly different words:

Doubt is evidence of a careful mind, a faculty to be respected, not avoided.

I've never met a person who deeply regretted doubting things.
posted by Strudel at 11:52 PM on April 30, 2015 [1 favorite]


If romance was completely based on only going after the smartest, best-looking, richest, most well-rounded person you can find, there would be two insanely perfect people in this world that would hook up and the rest of us would wank ourselves to death as we wept.

Attraction is weird and awesome and just flow with it, man. I try not to ask myself why my husband married a dried up old hag, I only know that he did and he is stuck with me. So, I make him his special pancakes on the weekends, give him head massages, and remodel his house for him in thanks. Hey, maybe that's what he thinks is sexy! See, that wasn't so hard. You have unusual and attractive qualities and he sees them. Just relax and let it take it's natural course.
posted by Foam Pants at 11:52 PM on April 30, 2015 [2 favorites]


For what it’s worth, he sounds really creepy and inappropriate to me. He sounds like he is pushing really hard for emotional intimacy with you, instead of letting it happen naturally. I’ve known a couple of people like that, and they all turned out to be bad news. If you’re both really excited about each other, then sometimes that stuff does happen fast, but it should be coming from both sides, and not just from his.

I also think that you should listen to your instincts about him. If something about him or about this relationship seems off to you, then pay attention to that. Don’t discount your instincts here just because you don’t have a lot of dating experience. You might not have a lot of dating experience, but you certainly have people experience, and dating is just people. So it’s not like your instincts, honed by 30 years of interacting with people, suddenly become invalid once you start dating.

But if he’s a creeper (or, a controlling abusive person), then he will probably be counting on the fact that your shyness and inexperience will make you second-guess your own judgement and that will make it easier for him to push you into doing stuff that he wants but you don’t.
posted by colfax at 5:44 AM on May 1, 2015 [10 favorites]


If you're not feeling it with this guy, then, you're simply not feeling it. You can't force it.

That said, your self-esteem sounds like it's low. You should probably work on that.

You're right about the gift thing not being sustainable. If he's as good of a guy as he thinks he might be, he'll respect boundaries and whether or not you even want a relationship.

Maybe you just don't see yourself with this guy? You can't control him, but you can control your reactions to what he does or doesn't do.
posted by PsuDab93 at 6:11 AM on May 1, 2015


What do I bring to the table, besides my relative youth?

You come across as extremely intelligent, and he is physically attracted to you even though you think you are "mousy" - he maybe likes a more natural beauty like yours. I bet he also likes the fact that unlike most women who interact with him, you are not falling all over yourself to impress him. I have a cousin who is very conventionally attractive and financially well off, and let's just say it completely amazes me how often I have personally watched women throw themselves at him in my presence: so he is therefore attracted to people who treat him like a human being, have really solid interpersonal boundaries, and don't come on too strong. Such as you.

Will he lose interest as quickly as he developed it? "Blowtorch" phenomenon?

Impossible to predict, but generally the older a man is, and once he's taken his online profile down, the less likely this seems to be to happen. However, I could see the power dynamics shift somewhat once you finally have sex with him. Right now he is the one doing the chasing, and you have more of the power.

Will he eventually stop showering me with gifts and daily attention? This doesn't really seem sustainable.

It depends. The thing is, folks don't seem to believe that awesome, giving men really do exist. They do, and they do sustain it over the long term. I'm married to a really successful and handsome man who initially pursued me like this, and now that we've been married over 10 years, no, I don't get little gifts everyday, but he does do something thoughtful for me each and every day.

To what extent is his hot pursuit fueled by the fact that I was reluctant at first? Physically, we haven't done more than a quick peck on a street corner. Will his interest dwindle away after he's "gotten" me?

It's true that rejection can be a pretty powerful aphrodisiac, but after 2 months and no nookie there has got to be something very compelling about you that he's seeing. Go you! Have you ever heard of the controversial (and often hated-upon) dating book for women called The Rules by Ellen Fein and Sherrie Schneider? Well, OP, by the way you've described your behaviors here it seems you happen to be very naturally "Rulesy," which is highly attractive to a certain cohort of hetero men. You have high standards for yourself. You are not the type of woman to be texting him constantly to the point of annoyance, and being too vulnerable too soon, and wearing your heart on your sleeve. You know how to say no, and live your own interesting life. In other words, you have good game and very healthy boundaries. I would not be surprised in the least if this man thinks you are "The One" for him and proposes to you within the next 18 months.

The real question is: are you enjoying these interactions?? (It seems like you are.) Is he worth your time? Do you want to get married in the next few years? If so, then just go with it. I don't really get where people in this thread are coming from with the "creepy" label here -- I get that AskMeFi has a bias against really rich, Alpha-ish guys but I have not seen any boundaries crossed here at all. He accepted your ending things and asked to stay friends and was 100% upfront about you maybe changing your mind and dating him again. He doesn't seem super eager to get in your pants. He calls when he says he will. The conversations are not all about him-- he's asking loads of questions about you and seems into you. Honestly? He seems like a catch IF and only if you are into his style. Good luck.
posted by hush at 7:27 AM on May 1, 2015 [4 favorites]


I'm with Michele and other posters that you are likely much closer to his "league" than you suggest ... but I think you may also be misjudging his behavior by the standard of the other men you're around.

I'd venture to guess -- and apologize if I'm wrong -- that you know a lot of men around your age, still struggling to get their careers going, nerds or ex-nerds as opposed to athletes, average looking, etc. For these guys, being with someone at or above their "league" has HUGE ego value. They have probably been trained through painful experience to try to be cool with women, because being overeager comes across as unappealing. Aggressively chasing a less attractive woman is basically the LAST thing they would think to do.

This guy is nothing like them. Someone who is handsome, athletic, successful, and forty has been successfully dating women in his "league" for 25 years, and there's a very good chance that it's just not as important to him. He's never had to fake being cool because his attention has always been received as flattering rather than trying too hard.
posted by MattD at 7:42 AM on May 1, 2015 [3 favorites]


There could be a lot of possible things with this dude:
* he's a future stalker
* he's a future abuser
* he's a future stalker/abuser
* he somehow has no social skills
* he's having his midlife crisis (SUPER likely)
* his eggs are rotting and he's desperate to make babies ASAP
* he's one of those dudes who's only interested if you're not and once you cave in/sleep with him, he'll leave ("blowtorch syndrome?" hah)
* he likes to be dominating and picks a "shy, mousy person" he can always get his way around.
* he likes "teaching and caregiving" and isn't looking for an equal to date
* he's somehow wandered out of a romantic comedy or romance novel by mistake.

Unless somehow it's the last one, which it probably isn't because who gets that lucky, in more cases than not this sounds too good to be true.

I do think leagues exist, but this guy might be more in yours because there's ah...something off with him. As a girl who's probably not totally dissimilar to you in some ways, I seriously wonder about the dudes who go after me because uh...there's usually something off and they end up not being decent. (But I'm a weirdo magnet.) I'd seriously wonder about his past relationships and exes and how things have ended. Does he get along with them, or have they all run screaming?

And in this case, there is something off: he doesn't take no for an answer. You wanted to stop dating after two dates and he not only is somehow still dating you, his first reaction was to give you a present? What? Yes, that's red flaggy. Hell, you've been dating for a few months and he bought you a yearlong membership? Huh? I tend to think that anyone who won't take no for an answer is going to run me over someday and I'd advise fleeing. (Then again, sounds like he'll just chase you.)
posted by jenfullmoon at 8:16 AM on May 1, 2015 [4 favorites]


Woman, listen. You can answer this question yourself if you stop diluting your awesomesauce. Seriously, build some self esteem. Then you'll get the feel for if he is really into you or if its some manioulation thing or whatever, but my god, you need to build some self esteem. Noone is "out of your league." Noone. Everyone is just some homosapien spending time somehow between eating, pooping, and sleeping. You probably stand out to him because in this time you have brainy or creative pursuits (just a guess from the theater date and book sharing). You are cool.

Now with you new super fortified dose of self esteem, does he know you're as cool as you know you are or does he think incorrectly that you are not as cool as you know you are?
posted by WeekendJen at 10:12 AM on May 1, 2015 [1 favorite]


I am going to pop in one last time to say that you need to worry a whole lot less about what he wants and what he is getting out of it and wonder what you want and decide what you are getting out of it (and whether or not that is worth something to you -- worth sticking around and dealing with him, your self doubts, whatever).

I spend time with men who take care of important needs of mine. I do my best to make sure they are well taken care of as well, but, I mean, if they don't like what I have to offer, they know where the door is. So I don't spend nearly as much time wondering what they want as I do wondering what I want and whether or not they are a good match for my needs and giving me what I want.

I have spent some time with men who were "out of my league." One was lots older than me. He didn't have money. He was out of my league in other ways. It was a growth experience. He had his own reasons for being interested in me (and I think it was a growth experience for both of us). I very much wanted the growth opportunity his interest in me presented. I wasn't happy with some things about myself and knowing him helped me become more of the kind of person I desired to be. I remember him quite fondly and I am very happy I spent that time with him.

I like men who are a growth experience. It's a challenge and it can be a lot of work and it's not everyone's cup of tea. Decide if that is your cup of tea. If so, that's fun in its own way, like getting a good workout or taking an interesting college class. If that is something you want, then enjoy learning to do this dance with him. If not, hey, go find something you do want.
posted by Michele in California at 10:32 AM on May 1, 2015 [1 favorite]


Being a guy, I find nothing wrong with spending a little money to make a girl happy even if it goes nowhere as long as he can afford it comfortably. And it sounds like he can.

And since he's pursuing you he definitely does not consider himself out of your league.

So, I guess I will ask you the question only you can answer...

Why do you consider yourself out of his league?
posted by kschang at 1:38 PM on May 1, 2015 [1 favorite]


There is some excellent and thought provoking advice above.

My question to you:

Instead of wondering why he likes you, have you wondered if you even like him, or why you like him?

This is not a one way street.

Do you enjoy spending time with him? When you're with him, do you feel stimulated, happy, at ease? Does he make you laugh? Do you have delightful, intellectual debates that stir you? When he's not around, do you miss him a bit? What is it that you miss?

Because if you're not in to him, independent of everything you have described above, it doesn't really matter if or why he is in to you. Don't choose to be with someone because you think that they chose you and now you have some duty to do the same.
posted by nightrecordings at 4:24 PM on May 2, 2015 [3 favorites]


Forget about being in a "league" and someone else being in a different, higher "league." It may genuinely be the case that he is attracted to you. Really. I'm a random person on the Internet, but trust me on this. In adult life there are no leagues.

Ask yourself instead if you're interested in him. I mean, don't focus on his interest in you. Are you interested in him?
posted by Pechorin at 12:55 PM on May 3, 2015 [1 favorite]


I would ask yourself if you even want a romantic relationship, especially given your lack of romantic involvement in the past (which I presume was somewhat voluntary, unless there's some bombshell there that you haven't revealed). I don't get the sense that you even want this to work out. Nothing in your question indicates that you want to date anyone, let alone this one guy, and it seems like the only reason you bring this up at all is that this guy is just so into you that he just won't let up no matter how little interest you show, no matter how much you reject him. It's almost like you're arguing that you should want a relationship with him based on these very objective, depersonalized measurements of dateability like wealth, being "conventionally attractive", successful, etc. Would there be any circumstances in which you would want the type of interest this guy is showing from anyone at all? If not, that is okay! It just seems like you're maybe jumping from "I am not interested in a relationship, an attractive man is interested in a relationship with me" to this very judgmental, self-deprecating place of "I do not deserve this attractive man" and I wonder if you are just trying to justify not wanting a relationship at all. Which is totally fine.
posted by deathpanels at 7:48 PM on May 3, 2015


What happens when you turn the tables and ask him in-depth questions about his family and his childhood and his dreams for the future? Give it a try and see.
posted by mareli at 9:37 AM on May 5, 2015 [1 favorite]


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