UGH!! I'm no Demi Moore

July 4, 2006 4:29 PM

Paging Mrs. Robinson: How should a lady gracefully discourage a Bright Young Thing who seems to have formed an inappropriate crush?

Here's the scoop. I have a circle of friends with whom I do a bike ride on a weekly basis. I like all of them, and over the past few months we've developed into a very close-knit group.

One of the guys recently started asking me out, and making it increasingly evident that he'd really like to get involved romantically. He's smart, gorgeous, we have tons in common, we both like the same stuff... so what the heck's the catch?! you ask. simply put: he turned 21 last month, and I turn 38 next month. I personally see absolutely no future for anything but a purely physical fling with this guy -- in the spirit of names-changed-to-protect-the-innocent, let's call him Bright Young Thing. I mean, sure maybe he's into a hookup, maybe he's checking the 'older woman' deal off his List, maybe this is a recent social fad. However, I'm not, and never have been a 'hookup' sort of person, nor am I in any way what one might consider a MI(Y)LF (being disqualified simply on the M portion, forget the rest). Nevermind the fact that I didn't date 21 year olds back when I WAS 21 as I seem to recall (most) guys that age being a huge pain in the tail. Plus I recently stepped out of a nearly ten year serious relationship (admittedly this has left me with a bunch of pages stuck together on the relationship front) AND the final fly in the oatmeal is that I've been on and off dating another (age appropriate) member of the same circle of friends.

In other words, There Be Dragons. Last week it all came to a head when Bright Young Thing asked me to dinner. Maybe I was just being dense or something but I figured it was a group deal so I accepted, only to discover he'd made reservations for just the two of us at one of the fancier sushi joints in town. During dinner he made it pretty clear what his expectations were and that he wanted to continue 'going out'. I kindly but firmly insisted on paying Dutch, kind of avoided the whole 'dating' question, kept things on the down low and left feeling decidedly awkward. Since then he's called several times, has been emailing and texting me, and only the fact that I was out of town camping on a mountain bike trip for the past week has kept me from having to say something. I'm due to meet these guys in a couple nights for another cruiser ride and I'm anticipating more awkwardness from Bright Young Thing... if nothing else he tends to sort of follow me around on the rides like a stray puppy... adorable but... yea. Right.

I super dig this guy on a platonic basis and if he were even ten years older I'd hit it all over town but... yeah. So far the only solution I've come up with is telling myself repeatedly 'he's young enough to be my son... he was born the year I graduated highschool...' and so on.

At the very least I don't want to embarrass this guy in front of the rest of our friends, and I really don't want to make myself scarce in their group because I truly enjoy hanging out with ALL of them. They're a pretty openminded and mature bunch, but I just don't want any unecessary drama b0rking the vibe.

So anyhow, what sort of wisdom does MeFi have to impart on navigating this mess?

-- thanks much, LFR

posted by lonefrontranger to human relations (56 comments total)

Interesting that in your whole story you never once said that you have told him you're not interested. That might be a good first step. It doesn't sound like he's done anything wrong, or that his crush is 'inappropriate,' and how you felt about 21 year-olds when you were his age has nothing to do with it either. 'Sorry, I just like you as a friend,' has a long and fairly successful history as a nice way to reject someone.
posted by bingo at 4:34 PM on July 4, 2006

uh, yeah... sorry I did forget to say that, yes - I have tried to politely tell him a few times 'no, I'm not interested'. He seems to not really be listening... in fact he gets a little bit defensive by saying 'well I know you are open to dating "Age Appropriate Member of Group", so what's the matter, do you think I'm too young?!? (to which I responded 'Yes!', to which he retorted 'that's not a real reason!'.

The true challenge is that I AM attracted to him, but I just can't go there. Add the fact that I don't want to embarrass him in the midst of our circle of friends and this kind of derails me becoming any snarkier or more determined to get rid of him.

it's kind of not cut and dried here. sorry I wasn't more clear.
posted by lonefrontranger at 4:42 PM on July 4, 2006

I'm with bingo; have you simply told the guy that you like him but it just isn't going to happen? You talk a lot about avoiding him but not at all about him ignoring your requests that he stop. Which leads me to believe that you haven't asked him to stop.

Unless you've told him flat-out that you aren't interested, he isn't doing anything wrong. And as long as you don't do it in public, why would it embarrass him in front of your friends?
posted by Justinian at 4:45 PM on July 4, 2006

Sorry, I failed to preview. Guess that answers that. If he ignores repeated insistence that you aren't interested he has moved from "cute young suitor" to "annoying pest."

Tell him what you've told us; that it plain and simple isn't going to happen and that he is making you uncomfortable and if he continues it is going to mess up the group of friends. If he STILL continues, there probably isn't much you can do to prevent him from getting embarrassed in front of your friends; but in that case he is pretty much asking for it.
posted by Justinian at 4:48 PM on July 4, 2006

That last exchange you shared makes your BYT sound like a bit of a jerk, or just very thick headed. At this point maybe you should tell him that if he doesn't back off a little, he's jeopardizing your friendship. His whole argument sounds a little immature as well; dating one person doesn't mean you're open to any dating opportunities and age is as valid a reason as any not to go out with someone.
posted by MadamM at 4:48 PM on July 4, 2006

Okay, so he knows that the age thing is an issue for you, and he's trying to wear you down. But is it really the "Age" issue, or the feeling that he won't commit? If it's the second, I say that's pretty reasonable. You can't expect a 21 year old guy to commit to an older lady, Tell him that you are looking for a real relationship and a real relationship only. To make the point, you could tell him that you'll date him for one year with no sex.

The point here isn't to go a year without sex and then have a long term relationship, it's to scare him off with the threat of commitment guys are afraid of commitment, so you can use that to your advantage.

On the other hand, if it's just the age thing, well, my opinion is that you should just do it and have some fun. Enjoy life. Get over your taboo and have some fun.
posted by Paris Hilton at 4:55 PM on July 4, 2006

You need to talk with him about this out of earshot of anyone else. I recommend that you just tell him something simple, like "It's not right for me," or "I'm not feeling it." "I like you as a friend" is fine, too -- even though some people scoff that it's a cliche, the real meaning is, "I'm not going to date you." In fact, you could just say that: "You're great, but I'm not going to date you."

If you give him reasons, he's going to try to persuade you. About the age issue, about the likely awkwardness, about the on-and-off nature of your involvement with the other guy... any reason you might give.

Be firm, and then stop talking. No explaining, no apologies, nothing. If he persists, take him aside again and say the same thing.
posted by wryly at 4:57 PM on July 4, 2006

Disclaimer: My opinion on this might be a little different because I was twenty when I moved in with my wife, who was 29 at the time. Six years later, things have worked out fucking awesomely.

Other disclaimer: I'm going to be blunt.

It sounds like this question boils down to context that cannot be communicated through simple text. Before you shut out your younger admirer completely, there are two considerations: first, if you tell him that you're not ready for a relationship, but interested in sex, it's not like any 21-year-old male will turn you down. Secondly, at the risk of being extremely rude, you're unlikely to have many more opportunities to fuck a hot 21-year-old.

So, as I said, context applies here:
How hot is he, really?
How good a relationship could you see yourself forming with the person who's your age?

I ask because male sexual territoriality being what it is, it's likely that unless BYT is extremely mature for his age, he will strut. That same territorial nature is your way out, by the way - imply that your relationship with the other man is slightly more solid (emotionally solid - don't lie in a manner that could backfire on you) than it really is. Your being unavailable by reason of being already taken is about the only way you're likely to end this without drama.
posted by Ryvar at 5:01 PM on July 4, 2006

You really need to get over the whole age thing. If you'd go for it if he was ten years older, why not give it a try anyway? What's the worst that can happen? Just let go of your preconceptions and hangups, and see where it takes you. At least you'll get to try something you've never tried before.
posted by reklaw at 5:02 PM on July 4, 2006

i dont really see what the problem is in this case. you are both adults and if you like each other why not act on it. emotional intelligence rarely depends on the year you were born. i know sixteen year olds that have more wisdom and security than my parents. he could be an old soul and you could be a child at heart. so whats the problem? if you are hung up on the perceived social taboo of the situation try to keep in mind the golden rule of being happy-- dont give a fuck what other people think
posted by petsounds at 5:04 PM on July 4, 2006

Ah. I didn't preview either. If you've already had that exchange, then yeah that changes things completely. I still suggest overstating your interest in person B as your way out of this.

in fact he gets a little bit defensive by saying 'well I know you are open to dating "Age Appropriate Member of Group", so what's the matter, do you think I'm too young?!?

Yeah. This was (and in future exchanges will be) your way out: tell him "It's not even so much your age as it is that I'm dating AAMG."

Also:
That last exchange you shared makes your BYT sound like a bit of a jerk, or just very thick headed.

No, it makes him sound like a young male, speaking as an only slightly-less-young male. Age isn't really a good reason to him, and it wouldn't be to me, either. You being unavailable would be, though, and if he's at all a decent sort he'll respect that.
posted by Ryvar at 5:08 PM on July 4, 2006 [1 favorite]

You being unavailable

Sorry, LFR being unavailable
posted by Ryvar at 5:10 PM on July 4, 2006

Hey if I saw you ride by on that Bianchi fixie, I'd be into you too, Mrs. Robinson!

OK, seriously...sometimes boys, especially persistent ones like this one, need to be told firmly and in no uncertain terms to back off. Tell him that if he continues to pursue you then he will be jeopoardizing the friendship which you very much enjoy with him.

He may just be 21 but he's a big boy now, so you be straight (but fair) with him and let him be responsible for his own emotional welfare.
posted by randomstriker at 5:17 PM on July 4, 2006

The best way to make him get is to consistently say no in the simplest and most extremely casual manner possible. It's like when toddlers topple over, in that if a parent rushes over and makes giant fuss then the kid will take his cues from them and treat it like a giant trauma that it isn't. Don't treat his interest as traumatic and it won't be, for either of you.

That's if you are truly unconflicted about it, which I don't really believe. But either way, the bigger deal that you treat it as, the bigger deal that it will become.
posted by NortonDC at 5:25 PM on July 4, 2006

Jeez, 38 year-old single lady getting hit on by a 21 year-old hot type guy. It won't last but would having a fling be a bad thing? I mean, really. It may sound crass but hit it already. If it works out longer term, bonus. You won't statistically outlive him. If it doesn't, it was fun while it lasted.
posted by shagoth at 5:32 PM on July 4, 2006

"You're a nice guy, but, I'm afraid it's like that saying, you know, I'm 'not that into you'."

If you feel the need to elaborate, you can add,

"I realize we've gone out on a date, and we ride together pretty regularly. So I've had a chance to get to know you pretty well, and although -- as I said -- you're a nice guy, there's not any romantic attraction there. I'm sorry to have to be this blunt, but I thought it would be better for you to know that I'm not going to date you instead of stringing you along."
posted by La Cieca at 5:34 PM on July 4, 2006

Forgive me, but your writing doesn't exactly read like you're 38. If you're not attracted to this guy because of the way he acts, then fine. You can steer clear of him in the usual way, for the usual reasons. But if you are attracted to him yet are avoiding dating just because you feel his age is not "appropriate" then that's rather sad.

When I was 15 I dated someone 16 years older and have continued to date people of significantly greater (and lesser) age. And I've dated a 20 year old with more depth and maturity than a 40 year old that I've dated. What counts is emotional maturity, not calendar age.

Regardless of which way it goes, he's going to be dumped time and time again throughout his life. He'll have to get used to it. Being dumped builds strength of character! So if you don't want to date him, say: "I don't want to date you. Maybe sometime we'll be friends, but not in a romantic way". Or if you do want to date him, say: "I'm up for a fling, but this is never going to be something serious or long term."

Many men can cope with that kind of talk. Better than pussyfooting around with clichés and euphemisms.
posted by skylar at 5:50 PM on July 4, 2006

What worked for me was to look my own BYT right in the eye and say "Sweetie, it ain't gonna happen. I have shoes older than you!"
posted by Corky at 6:07 PM on July 4, 2006 [2 favorites]

I AM attracted to him... He's smart, gorgeous, we have tons in common, we both like the same stuff... I super dig this guy on a platonic basis and if he were even ten years older I'd hit it all over town but...

... but women can be such masochists? :)

If age is the one and only thing that is stopping you, then Bright Young Thing is right, it is not a good reason. Besides, the difference is not even as dramatic as you make it sound. And it isn't a Mrs Robinson situation.

Anyway, since you say you are positive you don't want to go there and are only looking for ways to make him understand that clearly, then I don't see what can be done other than a) tell him very bluntly, which hasn't been very successful so far, or b) just stop being around him, which doesn't sound possible, or c) make an effort to ignore his flirting while still behaving to him in a friendly manner like before, so you can keep enjoying the same circle of friends and activities and so on. It will be awkward but sooner or later he'll get tired of it when he sees it's going nowhere.

If he is not convinced, though, it's probably because he's picked up the fact you are indeed attracted to him. I don't see how to get round that, other than give him some other generic reason, or expand at length on why you have such mistrust for gorgeous, smart 21 year olds just because they're 21, but I don't see the latter going down too well.
posted by funambulist at 6:08 PM on July 4, 2006

If the age difference is the only thing that's keeping you from dating this guy, I don't see what the problem is. My brother's wife is 16 years older than he is, and they've been happily married for about 8 years now. Including the dating period, they've been together for about 10 years. Just sayin'.
posted by misozaki at 6:15 PM on July 4, 2006

Ryvar, wryly, La Cieca, and Paris Hilton, thanks. this helps.

Corky: Best. Answer. Ever!! love it, and I can actually use it, too.

it should be patently obvious by now (re: skylar's commentary) that I'm horrible at this type of communication thing. I realise age has nothing to do with maturity. in this realm I am basically stuck at about fourteen myself.

remember also that I'm pretty recently out of a ten year relationship and so I'm tremendously out of dating / Meet Cute practice and pretty much a mess in other ways.

honestly it's a combination of things, as I said. there is no cut-and-dried. I'm NOT ready for a relationship, really, of any sort. I've only recently come to this conclusion myself. this is (well mostly) the driver behind the off-and-on nature of dating AAMG.

frankly I suck at dating. I hate it with a passion. And yes there is a lot of attraction with this guy so absolutely (cheers NortonDC) yes, I'm conflicted. but I just wanna be friends. I know anything romantic with him has a high potential to get messy. I think you all stated it pretty clearly and I should just be honest with this guy. The thing that got me stuck was that I remember being that age myself and painfully sensitive about this kind of thing. I do like this guy, I don't want to leave bruises, but yea, it's a life lesson.

Reklar wrote: Secondly, at the risk of being extremely rude, you're unlikely to have many more opportunities to fuck a hot 21-year-old.
haha absolutely true dude! that's not rude, it's a fact, no worries on being blunt. I totally know I've hit (if not passed) my sell-by date. which on reflection is likely what makes this whole thing so bloody tempting. but I just can't go there.

I think a lot of people here really clarified it. I (having never been a Hot Young Male) wasn't really thinking it through in those terms. I bet this guy already KNOWS he can leverage his hotness. Yes, he is very, very hot, and from what I can tell he's pulling the girls out of his hair on a daily basis. so in my (admittedly this may be cynical) opinion he's using all that pretty young male sexuality / arrogance to pressure me (an easy mark?) into caving. I know he's not doing this in a malevolent way, because that's not his personality. he's just doing it because he can.

Sigh. yes, this is now absolutely reminding me why I didn't date 21 year olds when I was that age. Major. Pain. In. The. Tush. (not to insult any of the young male element here... but jeez).
posted by lonefrontranger at 6:29 PM on July 4, 2006

I dont know if this has been covered but if you do hook up with him and you are both part of the same group of friends, there is the possibility of weirding out the rest of your friends, which could easily happen in this imperfect world...
posted by GleepGlop at 6:39 PM on July 4, 2006

The truth about males, and especially males in lust, is that we're typically rather thick when it comes to understanding communications. Especially communication from those for whom we lust.

So use Very. Small. Words. Be Direct. Do Not Waffle. State Things Clearly. Use Capital Letters When You Speak. Speak Slowly.

It'll help, a lot.
posted by five fresh fish at 6:40 PM on July 4, 2006

GleepGlop wrote: I dont know if this has been covered but if you do hook up with him and you are both part of the same group of friends, there is the possibility of weirding out the rest of your friends...
Bingo! that's probably Reason Numero Uno why I'm really freaked out about this. I just don't need the drama.

and yea, I know I'm mostly internalising the drama unto my own situation but IME perception tends to equal reality in a depressingly large proportion of social situations.
posted by lonefrontranger at 6:54 PM on July 4, 2006

If age is the one and only thing that is stopping you, then Bright Young Thing is right, it is not a good reason. Besides, the difference is not even as dramatic as you make it sound. And it isn't a Mrs Robinson situation.

Age isn't, but maturity is. I'm a 26 year old guy that works on a college campus full of 18-22 year old cute little thangs. Which is great for my dating life, except for one thing: They're so frigging immature and really have no clue about ANYTHING that it's nearly impossible to date them. Actually, it's possible, it's just incredibly painful to date someone who has yet to graduate college and live for a while on their own.

So while some may go, "What's the problem?" ... it's a lot of work for the older member of such a relationship to keep their patience and keep from condescending. At least, it is for me.
posted by SpecialK at 7:26 PM on July 4, 2006

The truth about males, and especially males in lust, is that we're typically rather thick when it comes to understanding communications. Especially communication from those for whom we lust.

So use Very. Small. Words. Be Direct. Do Not Waffle. State Things Clearly. Use Capital Letters When You Speak. Speak Slowly.

Nail. Hammer. Bang.
posted by jason's_planet at 7:30 PM on July 4, 2006

Tell him what you've told us;

Don't do this!

Whatever you tell him has to be blunt. Absolutely no equivocation and no discussion; those will just look like maneuvering room to him.
posted by Chuckles at 7:30 PM on July 4, 2006

17 years is a big gap. Maybe not now, but someday. Trust me. I'd recommend against anything, even a little fling, because you don't know where it will lead.
posted by pmurray63 at 7:44 PM on July 4, 2006

If he was 24, I'd tell you to go for it.

Wait til he gets through his post-college crisis and then reconsider.
posted by k8t at 7:56 PM on July 4, 2006

those will just look like maneuvering room to him.

+1
posted by SpecialK at 8:05 PM on July 4, 2006

Nevermind the fact that I didn't date 21 year olds back when I WAS 21 as I seem to recall (most) guys that age being a huge pain in the tail.

And you wonder why he wants to date an older woman ... (this is not to say that you should date him, just that I can definitely see the frustration when 21 year old women are so often unavailable).
posted by spaceman_spiff at 8:13 PM on July 4, 2006

I must also add: Leave him no hope at all.

If there is even the slightest hint of a whisper of a vacillation in your response, you lose.

It's a binary brain, and anything that is not entirely Off is, of course, On.
posted by five fresh fish at 8:16 PM on July 4, 2006

I dated a 38 year old woman when I was 21. I'm 39 now.

I'm not going to try to draw specific parallels, but I will say that this guy has no idea what you're really like. I don't care how good a game he can talk or how cut he is. He could be a friggin son of one of your high school classmates, basically. He's an embryo who can ride a bike.

Your hesitation in engaging with him is completely sensible. Listen to yourself.
posted by sacre_bleu at 8:31 PM on July 4, 2006

five fresh fish is spot on. Though it might be handy to really work out exactly what it is that you want first.

It looks like you're taking his age alone and assuming he can't be what you want. You're *probably* right, but that uncertainty is probably why you're here.

If you lay out exactly what you want from the sort of relationship he's headed towards it will give him a fair go at deciding if he wants to continue courting you. And his reaction will give you a bit more information with which to make your decision.

(Though I do know that the age difference can throw you pretty badly. When I was looking at a relationship with someone not a lot younger than me I was shocked when she didn't know of "Who's on first". Made me feel old.)
posted by krisjohn at 8:39 PM on July 4, 2006

Heh. The hardest part with age differences in relationships from what I understand is the difference in sense of humor. My sister's 22, and I'm 26. She and her friends have a completely different sense of what's funny and what's not than I do, and sometimes it can lead to "Oh my god, she doesn't get that" or "Oh my god, he's such an old fuddy" moments.
posted by SpecialK at 8:41 PM on July 4, 2006

in fact he gets a little bit defensive by saying 'well I know you are open to dating "Age Appropriate Member of Group", so what's the matter, do you think I'm too young?!? (to which I responded 'Yes!', to which he retorted 'that's not a real reason!'.

I sort of agree with him.

My mother has been happily married for 10+ years to a man seventeen years her junior. As k8t pointed out, though, a few years might make a difference; he was 24 when they met.
posted by geekyguy at 9:28 PM on July 4, 2006

in fact he gets a little bit defensive by saying 'well I know you are open to dating "Age Appropriate Member of Group", so what's the matter, do you think I'm too young?!? (to which I responded 'Yes!', to which he retorted 'that's not a real reason!'.

I think I agree with him and with geekyguy. My mother has been married to a guy 15 years her junior for almost 20 years. He was also 24 when they met.
posted by zia at 10:22 PM on July 4, 2006

On preview, big oops! They have been happily married for 30 years!!!
posted by zia at 10:23 PM on July 4, 2006

Zia; Geekyguy: Speaking as a guy, there are miles and miles and leagues of difference between a guy who's 21 and a guy who's 24. We're talking astronomical units here.
posted by SpecialK at 10:59 PM on July 4, 2006

Rent "How Stella got her groove back".

Two reasons:

1. Subject matter is relevant.

2. It's an absolutely woeful film; after forcing yourself to sit through that, you'll have no trouble doing the exact opposite of what the film suggests is the Right Thing :-)
posted by flabdablet at 11:21 PM on July 4, 2006

Your tone suggests that you are flattered by the attention (who wouldn't be?) and you may have done the mild flirting thing, consciously or not. If you shine even just a bit brighter when he rolls by he's sensing it. It's not just "dense" to accept a dinner date with those vibes between you without thinking through the implications -- it's weird. You've been out in the world for a while. When a man asks you out, you figure out with a few simple questions what he's got in mind before you say yes. Pardon the armchair psychologizing, but everything you're describing strongly suggests that there's a not-so-small part of you that wants what your conscious knows it shouldn't have -- a hot date with a hot young man. He's sensing that you're torn and hoping he can push you over the edge.

Whatever the case, if you've already told him you don't want to see him and he's ignoring you, then you've already tried to end it gracefully. Now it's time for the small. emphatic. words. that others have mentioned. Be honest and firm. Acknowledge that you're flattered, acknowledge that you may have sent him mixed signals with your actions, and tell him if he keeps asking you out you're going to feel too uncomfortable to remain friends and that you don't want that to happen. Until you are crystal clear with him he's probably not going to stop. If you're not entirely sure you want him to, and you think you might give in to your feelings despite your better judgement -- well, don't leave your riding group, but take a break. Let the fire die a bit. Whatever you do, you have to be clear and determined in your own mind before you'll be truly convincing to him.
posted by melissa may at 11:34 PM on July 4, 2006 [1 favorite]

Do you really want to risk having a restaurant hostess ask if you and your son would like a table?
posted by Cranberry at 12:42 AM on July 5, 2006

Well to be fair the followups clarify this isn't *really* all about the age difference, so nevermind that angle (and sorry about the 'masochist' joke! it was silly and half-hearted anyway but I realise it is a different situation), it's the 'I'm NOT ready for a relationship, really, of any sort' you need to convey to him in the bluntest possible terms, as others already said.

Something like the phrasing La Cieca used, maybe even a bit more 'aggressive'. I don't think a simple one-off talk is going to solve it, it sounds like he'll still try and use every opportunity to flirt with you, but every time he does it, just be confident, turn off any sign of attraction to him, and send a very clear 'cut it out, it's not going nowhere' message. There's only so much obstinacy any man, at any age, can bear. You have more patience, use it to your advantage!
posted by funambulist at 2:39 AM on July 5, 2006

you mention that you never dated these kinds of guys (cute, attractive) even when you were younger. it's pretty obvious that you think that you are using your past rejection and abstinance as your crux for attraction and as relevance for the possibility of a relationship. your leverage is that you feel finally validated as worthy in the eyes of this younger man, and are using him as a collective representation to get back at those BYTs that never gave you the time of the day when you were younger. it's pretty obvious. kind of like the dumpy, middle-aged southern housewife who was never got onto the cheerleading team, and then obsessively pushes her own kids to pursue the life she never had. bad metaphore, but you see where i'm coming from.

this guy you are attracted to clearly has 'game', if he tricked you into a date alone, has girls that you say he is 'pulling out of his hair' constantly, etc...and you clearly are falling for it.

therefore, be warned that even if you use the 'sorry little man, but i'm looking for someone to date who will commit to a long-term-relationship', please be warned that he will probably have no qualms lying to you and telling you that he's indeed up to the task of committment. which he just can't do at 21, i'm sorry. the chances of finding a 21-year-old player (like him) that wants to honestly commit to a 'pushing 40-year-old' woman is woefully slim. please don't fool yourself. this kid is clearly playing you hard. it's clearly a game to him. back away now if you want to save your sanity. don't be "that lady". at 38 years, you should just have more common sense when it ocmes to realistic and pursuable relationships.
posted by naxosaxur at 2:59 AM on July 5, 2006 [1 favorite]

Past your sell-by date? Ouch. I'm 50 -- I better go wake up my 33 year old man and let him know I've expired!
posted by thinkpiece at 4:34 AM on July 5, 2006

kind of like the dumpy, middle-aged southern housewife who was never got onto the cheerleading team

Ouch, 'bad metaphor' is a euphemism here...

Besides, she said *she* was the one not to give the time of day to 21yo even when she was 21, not the other way round.
posted by funambulist at 4:37 AM on July 5, 2006

Well, the age difference is only an issue if you let it be one.

But in my mind, he's edging the line from "cute and flirty" to "stalker."

I think you need to lay it on the line before the next ride. Say that you are happy to hang with him as a member of the group. But anything beyond that is not going to happen. Tell him that all the emails, phone messages and text messages are becoming creepy. If you must play the age card, you can say that he needs to learn to accept rejection gracefully.
posted by KirkJobSluder at 6:01 AM on July 5, 2006

A couple of ideas:

a) Maybe the age-appropriate guy you've been dating "on and off" asked this guy to ask you out, see how far you'd go, just to see what your deal was. Men do this kind of thing.

b) Nothing you've described has been inappropriate on his part. You're both adults and he didn't force you into anything nonconsensual. If you didn't want to have dinner with him alone at a fancy restaurant, the right time to disclose that was before you sat down.

c) Your question is a long six paragraphs. That's an awful lot of text to sum up the idea, "I don't want to date this guy. How do I break it to him?" Because either you are or are not going to date him, and the outcome of that decision is all you need to convey to him - clearly - and most certainly not the reasoning behind it.

d) When you do decide exactly what you want - and I wonder if maybe you haven't quite yet - be very clear about it. Get on message and stay on message, and if he puts you in a position where you're forced to embarrass him, do it. He'll learn - he's still young.
posted by ikkyu2 at 9:53 AM on July 5, 2006

You do like him. That's your problem, your issues, not his. He's just doing the same wear-down move that works time and time again. There is nothing wrong with that in my book, unless it moves to stalking, but this doesn't seem like that.

4 things. (1) work out what you want first. If you are curious, then go on another date. Don't dismiss him out of hand. (2) Methinks that the fact that he can't have you is very much driving his attraction to you. Going on another date with him might make that go away. (3) This 38 year-old thinks that you should take dating less seriously right now because of your issues. That means being more ready to date, but taking it less seriously. (4) Don't worry about hurting his feelings. They are probably already hurt and rejecting him is going to hurt them more. I've seen (and been part of) millions of these situations. I want a woman who is not interested in me to communicated extremely clearly, small words and all. I prefer getting hurt to not knowing.

Sounds like your eyes are saying yes. Just say a small yes and you will be fine.
posted by Ironmouth at 10:45 AM on July 5, 2006

I know anything romantic with him has a high potential to get messy.

Isn't that true of any kind of romantic situation?
posted by qvtqht at 6:45 PM on July 5, 2006

Given this last batch of messages, I'm gonna yack again:

Your biggest challenge at this point is that you want to do it — and he knows it. Chances are you're one of those women who flirt without even being remotely aware of it.

Good luck. Even with the Small Words and Capital Letters and No Wiggle Room Whatsoever, your body language is probably going to sabotage your efforts.

You might want to seek advice on flirtation... or, rather, how to not flirt. You simply will not believe the subtleties and nuances that trigger an unconscious reponse in men.
posted by five fresh fish at 7:24 PM on July 5, 2006

MMMmm mmmm mmmm!

I dated a younger guy last summer and it was the best thing I ever did...hit that shiz!
posted by skjønn at 1:42 AM on July 6, 2006

five fresh fish wrote:

Your biggest challenge at this point is that you want to do it — and he knows it.

yea I am certain this is the case. the simple matter is that I'm conflicted and I'm sure I've been sending him mixed messages. I've always been terrible at telling people how I feel about them. One guy I dated awhile back told me I was the most impossible person he's ever tried to 'read'.

it's because while I LIKE guys, and enjoy their company on a platonic level (fercrissakes I was raised and socialised by a bunch of dudes)... I completely fall down at expressing any kind of non-platonic interest in men. so when I am attracted, it's like... I get all weird I guess.

like I said my guess is that while I'm 38 chronologically, I'm probably about fourteen on the dating intelligence metre... ack.

I also did appreciate all of you who rooted for the 'hit that already!' option but I'm afraid that's just not my nature. sure call me uptight but whatever. yes, it's tempting, very tempting, but no. I just can't go there.

the Gang and I are all meeting up tonight. at some point I've determined that I will have The Talk in private with BYT. I will use Very. Small. Words - and possibly Corky's awesome quote as well.

god I suck at this. *whingey tone* why can't we all just be friends?!?

you have been bang on the mark with every comment there five fresh fish. thanks.
posted by lonefrontranger at 1:02 PM on July 6, 2006

SpecialK, I hear ya. I'm 28 and working on a college campus. The 21-year-olds were NOT cute when I was that age. Now that I'm too old for 'em, they're all adorable, and the guys my age are all married/engaged/impregnating. Bleah.

When I was 21, I was dating a 29-year-old and he got so fed up with me he swore he'd never date younger again- then dated someone 8 years older than HIM. Now I understand that at age 21, I should have been dragged out into the street and shot for my stupidity! :P

Anyway, back to the topic. LFR, I think you're going to have to take the harsh route here:

(a) Tell him up front you will NEVER date him. In fact, be mean about it. Don't be gentle, don't let him down easy. He is not listening to your no's already, and it sounds like your body language is already saying "yes, yes, yes" whether you want it to or not. So, you may even have to be insulting. Tell him you don't respect him, kick him in the crotch, something.

(b) After this, avoid the hell out of him. Yes, that means giving up the rest of the group. You can't avoid drama regarding him at this point unless you drop everyone. He's already created the drama for you. It's been my unfortunate experience that some guys (i.e. the ones in denial, which this one is) won't get over you until you're out of sight for awhile.

It's an ugly solution, but the nice route hasn't been working, so...
posted by jenfullmoon at 4:51 PM on July 6, 2006

kick him in the crotch

I was thinking about saying this too, but it died during editing. It won't feel like you are being nice, but it may actually be the most kind and sensible solution available.

Another deletion that might be worth reviving.. Perhaps you should skip a meeting, giving whatever convenient excuse you can think of to the group. Then tell him in private that it is his fault, that he is irritating and angering you and you just didn't feel like dealing with it that day. Then again, maybe it wasn't worth reviving :P
posted by Chuckles at 5:31 PM on July 6, 2006

You guys have got it all wrong. Allow me to quote Rita Rudner:

Getting rid of a man without hurting his masculinity is a problem. "Get out" and "I never want to see you again" might sound like a challenge. If you want to get rid of a man, I suggest saying, "I love you, I want to marry you, I want to have your children." Sometimes they leave skid marks.

It works both ways - every girl I thew myself at when I was 21 ran screaming, too... although that wasn't my intent.
posted by mikewas at 8:23 PM on July 7, 2006