Help me not mess this up.
December 2, 2008 11:53 AM   Subscribe

Pursue him or leave him be?

I met a guy in my parents' hometown on a Friday in mid-October. He asked for my phone number, called the next day and we went to the movies. It was nice. We both live about an hour or so (opposite directions) from the town we met in, which is also his parents' hometown. We e-mailed a decent bit the week after, but things got quiet. It is worth mentioning he is a first year law student and is taking it VERY seriously. It is also worth mentioning that he is 25 and has never had a girlfriend.

He (we will call him Joe) e-mailed me a rather longish, unsolicited message on Nov. 10 and we ended up hanging out four times in seven days over the Thanksgiving holiday. He is nice, attentive, introduces me to his friends who all seem to know that we are "dating." In fact, one of his friends said to me, "So Joe tells me you are good people." So, that seemed promising. Also, Joe's younger sister seems to know all about us and basically told me he's never had anyone serious and she's rooting for us because he's a great guy. So yeah, that seemed good too.

There has been one problem, despite the fact that Joe has paid for movies and beers (I've bought him a few too) and sticks by my side when we're out, he is not physically affectionate AT ALL. The second to last time we hung out (after all those dates that ended with a hug and a kiss on the cheek), I finally kissed him, I mean really kissed him. He seemed so timid. (But I will admit, my last few smooches have been with really, really aggressive guys.)

The day after "the kiss," he didn't return a text message I sent him, which was odd because he was usually good about this. I called, he didn't answer but I left a voicemail seeing if he wanted to get coffee. He called back and we went. We had a good conversation for 90 minutes just about life and nonsense -- nothing about us. He got out of the car, hugged me, kissed me *near* my mouth. I said, "Good luck on finals." And he said "Oh those are two weeks away." And I said, "Yeah I guess we'll be in touch before then." We had previously talked very casually about getting together over Christmas. But I couldn't help but notice some distancing vibes from him. I have not spoken to him since he got out of my car. This was Saturday night.

Internet, I DO NOT WANT TO MESS THIS UP. I like him. He is good. I know what will happen, will happen, but I would like VERY MUCH to nudge it a good direction.

-How do I not scare him?
-Should I initiate a hangout soon? As in, maybe we can meet for dinner on a night he needs a study break? As in, hang out before Christmas?
-Should I just leave him be?

Internet, you are nice. I know you hate these questions, but I have a good feeling about this one. I don't want to scare him away, but I don't want to let it fizzle either. Help me balance this.
posted by als129 to Human Relations (31 answers total) 4 users marked this as a favorite
The Internet says, go for it. Life is too short to wonder if.
posted by poppo at 12:09 PM on December 2, 2008 [1 favorite]

As an awkward guy who finally had a real relationship after he was 20, the firsts can be daunting to rather scary. I had no idea what to do, and when things were appropriate. Can you call his sister? Or maybe his friends? Maybe they'll know more about what he's thinking.
posted by filthy light thief at 12:17 PM on December 2, 2008

Should I just leave him be?

The guy is 25, never had a girlfriend. All types of red flags right there. Sure, some folks are wall flowers, shy, timid, and don't know how to approach or pursue women, but once it happens, it happens.

So here this guy is, inexperienced, but with a woman who is interested and actively perusing him both emotionally and physically and he is still a cold fish, odd in his behavior even.

Maybe he is gay? You remarked (strangely) that he lives in the same town as his parents, maybe there is tremendous pressure on him to act straight, or to try to be straight?

But I really don't want to go down that road as it is such an incredible long shot.

Is he a virgin? More than likely he is uncomfortably physically, insecure of his body or his physical attraction. I mean, think about high school boys: they behave like this guy is behaving. Unsure what to do, unfamiliar with kissing, uncomfortable with making advances.

Could be he is so inexperienced that he still has a tremendous learning curve. Added to this is the possibility that he may himself feel like a freak, a failure with women, unattractive, and the like.

The good news is that once you jump his bones he'll probably be fine, in fact, you may not be able to keep him off of you...

I say that you should pursue things with him, take the initiative, and make it clear that you want to get physical with him. Don't leave in room for doubts in his mind. Invite him over for drinks and a movie and bed him.

Be aggressive. Some guys actually like that...


Yes, this is your one shot ever at happiness. A lawyer? Are you kidding? You don't get a second shot at babying up with someone in that line of work! Better not screw this one up!
posted by wfrgms at 12:17 PM on December 2, 2008 [1 favorite]

Could he be a virgin? If he's extremely shy and never had a girlfriend at 25 then not scaring him may not be on the table. The whole situation is probably terrifying. I was cripplingly shy when I got my first girlfriend (at 18), sure that I was bound to make a mess of any sort of physical contact. And, of course, I did at first. All I've got to work with here is memories of how I felt way back then, but I'd say you should just move slowly, laugh easily, don't take the situation too seriously. Send a lot of "you're doing fine" vibes. Keep pushing that envelope a little, but in a fun rather than a high-stakes sort of way.
posted by jon1270 at 12:19 PM on December 2, 2008

He has finals in 2 weeks? I wouldn't contact him to chat, but I would send him a care package while he studies. Cookies or coffee brownies?
posted by spec80 at 12:22 PM on December 2, 2008 [1 favorite]

Talk to him and tell him what you want and need from a relationship.
posted by Brandon Blatcher at 12:25 PM on December 2, 2008

Response by poster: I really think he might be a virgin, but I do not have that confirmed. But all signs point to yes, virgin.
posted by als129 at 12:29 PM on December 2, 2008

I'm a big fan of being honest about these situations. There's a risk that you aren't "playing the game" the way its "supposed to be played" if you tell him that you like him and that you aren't sure what he feels about things. But his behavior indicates that he is in way, way over his head and that he probably has no idea what to do. So just be straight up in a non-confrontational way and compliment him a lot when you talk the matter over. Tell him that you are attracted to him and that your feelings for him are making it difficult for you to not want to kiss him more. If he starts to back off, don't get too defensive, let him know that whatever his issues are, you'd like to have some fun working them out.

He sounds really scared. Make him feel comfortable and you will be just fine.
posted by Ironmouth at 12:33 PM on December 2, 2008 [1 favorite]

I'd say try to contact him again, gently - but also, try not to get too hung up on him, just to protect yourself a bit.
posted by 5_13_23_42_69_666 at 12:33 PM on December 2, 2008

I don't think you can mess this up. Either it's screwed or it isn't. Either he's gay/effed up/emotionally unavailable or he isn't. Sounds like he likes you in some way, and wants to hang out. If you can't warm him up it won't be your fault. You won't be able to fix him though.
posted by sully75 at 12:40 PM on December 2, 2008

He sounds nervous to me. But definitely interested. I would stay in touch - be warm and friendly and probably don't intiate any "serious conversations." Definitely call him or email, I bet he'll be SO relieved to hear from you. Then when you see him over Christmas, you can organize some *cozier* get togethers, which might facilitate more affection. Maybe watch a movie alone together at one of your houses? Oh yeah, and with finals coming up I wouldn't pressure him to get together before Christmas, but some contact to let him know you're thinking about would probably be appreciated.

And since you seem to want speicific advice, I think the right amount of contact would be one "item" of contact (text, email, call) two out of every three days. You want him to think about you frequently, but you don't want him to think he's developing a stalker problem, or that you have more invested than he does. I guess mostly just follow his cues on the communication, but don't hesitate to be slightly more aggressive than he is.
posted by robinpME at 12:41 PM on December 2, 2008

Ironmouth's advice is great, too!
posted by robinpME at 12:42 PM on December 2, 2008

Law school can be psychologically brutal, especially for people who noticeably take it seriously. He might be consciously distancing himself so as to not become too involved with you and take time from his studies. He is also likely very shy. Also, if he's in at a "good" school that's a pretty big ego boost for anybody for about the first semester. A combination of newfound confidence with complete social and sexual virginity, I would warn you. You seem invested in him more so than he you.
posted by norabarnacl3 at 12:43 PM on December 2, 2008

My brother was basically this guy. He used to agonize over those few nascent relationships that he did manage to stumble into, developing complex fantasies of how he had completely screwed things up. He was especially stressed when things turned physical at all, believing that he was doing things "wrong" and that his inadequacies were a turn-off to his prospective partner. The women he finally married essentially clubbed him over the head and dragged him home. I was thinking of him today because I happened to run into a women over Thanksgiving that he briefly dated years ago. We had a comfortable chat, catching up with tales of our mutual acquaintances. In the conversation, she told me that she regretted that it didn't work out with my brother, who was "sweet and kind." When I told her that he was quite upset that she broke up with him, she was baffled. From her perspective, he grew ever more distant until she "took the hint" and stopped trying. She denied ever "breaking up" or ever really having an actual relationship in the sense you or I would mean. Of course, he thought that he was screwing everything up and became more and more frightened, causing the whole misunderstanding. I remember him moping for weeks about how he mishandled the whole thing and had to laugh when I found out that he only needed to actually express his interest in order to keep things rollling.

Of course, I have no idea if this guy is the same as my fairly goofy brother or what he is thinking, but I do know that there are painfully awkward guys who have no clue what "signals" they are sending. If he is one of them, you have to abandon your well-honed system of hints and cues and make things abundantly clear. The worst case is that you have misread the situation and he has to explicitly tell you to back off. I have had more than one girl have that conversation with me -- it isn't that bad. Sometimes you have to make the extra effort to get the things you want.

Telling his baby sister and his friends about you is an extremely good sign. Nobody does that without having interest. I place way more emphasis on that than the ambiguous "distancing vibes." My guess is that he doesn't speak "vibe."
posted by Lame_username at 1:06 PM on December 2, 2008 [2 favorites]

Also, as someone who was married to a law student, the process makes the best of them a little bit crazy. I remember going weeks without a significant conversation with my lovely wife and that women could talk to a statue.
posted by Lame_username at 1:09 PM on December 2, 2008

Being shy is difficult. Being a "late bloomer," as a man, is difficult. Be patient with him, and be vocal. The problem a lot of shy guys have is that we have never developed the intuition that comes from the experimentation and experience that most people get in their teen years. It doesn't mean that we're defective (or closeted gays...), it just means that we can't tell when you want to be kissed.

Thing is, our society sends a lot of weird mixed signals about sexual things, and while most people with experience can basically cut through the crap to find their own way to a good time, someone who's older and inexperienced has spent his entire adult life feeling:
  1. Left out
  2. Confused
  3. Depressed
After all, if you turn on the TV, the talk shows and so forth are always talking about how everybody has sex, everybody has relationships, everybody everybody everybody; then you hear about abuse, dysfunctional relationships, sexual diseases... hell, even those Levitra ads can be depressing. "You mean sixty year old grandpas are still getting some and I am [2|3][0-9] and have never even gotten a sniff?"

To be honest, he's probably sitting around thinking about how much he likes you, how much he's screwed up, how scared he is, how he let a golden opportunity go by, and so forth.

God knows I've been there.
posted by sonic meat machine at 1:14 PM on December 2, 2008 [2 favorites]

So he was not affectionate, then you kissed him, then he initiated a sort-of-kiss. That seems like he is just really timid and freaked out, but making steps. I don't think you're messing anything up, just don't take his shyness personally.
posted by Solon and Thanks at 1:31 PM on December 2, 2008 [1 favorite]

Two weeks before law school finals in his first year?

He probably has lost all concept of time. What seems like two days for you seems like about 30 seconds for him. Keep this in mind.
posted by toomuchpete at 1:57 PM on December 2, 2008 [1 favorite]

I was in your shoes, once upon a time, with a shy guy who was finishing his surgical residency and was spending days at a time in the hospital from time to time. I went through all the same "will he won't he, is he, isn't he" sorts of stuff. It was driving me bonkers. More because of the mixed signals. I just had to know.

I couldn't trust myself to not blow it if we spoke face to face, so I wrote him a letter. Just poured out my heart to him on paper and told him how I felt. Gave it to him when the really horrible rotation he was on was over, and told him to read it. He did, and told me that he didn't feel the way I did. It was hard, but at least I knew. And life moved on.

We're still friends, btw, and you know what? After seeing him with the partners who eventually did come along when he had a bit more time and confidence and money, I think I'm really lucky that we're friends.

I don't think we could have been friends if I hadn't bucked up and just got things out in the open... eventually, it would have just gotten weird.
posted by Grrlscout at 2:19 PM on December 2, 2008

He doesn't know what he is doing yet. Dont be a source of added stress and confusion for him. Just relax, dont worry about it, if you are stressing yourself out it will come across and it will freak him out. Just be friendly and affectionate, and when you do see him next be forward and confident with him. Make him give you what you want without seeming needy, trust me I used to be that guy. (still sort of am)
posted by BobbyDigital at 2:33 PM on December 2, 2008

There are a LOT of guys who get anxiety when it comes to physical stuff. He sounds like one of them... I just think you should be pretty direct with him - counting on him to make the move or take hints probably isn't going to work.
posted by PFL at 3:05 PM on December 2, 2008

The good news:

You can't mess this up, unless you turn into total freaking stalker psycho chick and boil a rabbit in his kitchen. If you are yourself, your normal, sweet, nice, self, you will be fine.

He is going to need VERY clear signs from you. Very clear. It sounds like he is trying, but is scared/doesn't want to get into a relationship while in law school/doesn't know what to do...

...or he might not be into you.

But the only way you're going to find out is to just pretend you know how to do this and just be your normal, charming, self. Relax. Don't count the days. If you feel like emailing him, email him. If you feel like calling him, call him. Don't keep a calendar on your desk and mark it off, just be yourself.

The one caveat I would make is, make sure at some point you indicate to him that you understand how important law school is to him and how hard it is and what a time commitment it is and that you respect it greatly. He may still run fleeing from anything that could distract him but you could at least try.

[For the idiot who is making fun of you and condescending to you about this being 'your only chance' and making the sexist comment about 'babying up with a lawyer,' take a hike. I know what it's like to land a NICE guy and have your entire relationship history flash before your eyes. If you've kissed a lot of toads already, when you find a potential prince you want to not repeat every stupid mistake you've made. I get it. ignore them.]
posted by micawber at 3:19 PM on December 2, 2008

Wow. My gaydar is going off the chart here.

He doesn't sound shy. He sounds closeted, and it sounds like he's found his beard.

Sorry, but that's what I'm reading in your words.
posted by IAmBroom at 3:29 PM on December 2, 2008

Two weeks before law school finals in his first year?

He probably has lost all concept of time.

So I'm in this exam and we have to write the date on the answer booklet, so I ask the supervisor "what is the date, please?" and he says "it's the 15th" and I say "what month?"

I got the year right on my own, mind you, so it wasn't that bad.
posted by Mike1024 at 3:56 PM on December 2, 2008

I vote "shy." Pretend you are in an old movie--1940s perhaps?--and court him, slowly. (As for his being gay, I really don't think's 2008.)
posted by Carol Anne at 4:09 PM on December 2, 2008

i also think he's shy. the guy i'm seeing now, i had to initiate practically everything at first. if i hadn't read similar threads on askmefi about shy people, then i probably would have just given up. later on he told me that he was sure he had stuffed it up on several occasions, so the doubt thing isn't implausible either.
posted by sardonicsmile at 5:21 PM on December 2, 2008 [1 favorite]

Two weeks before law school finals in his first year? He probably has lost all concept of time. What seems like two days for you seems like about 30 seconds for him. Keep this in mind. posted by toomuchpete at 1:57 PM on December 2 [+] [!]

Pete reminds us ... this guy's studying for finals! You've got plenty of good advice upthread. Now let me ask you, beg you, to be utterly supportive of this guy until finals are over. Just send sweet messages or Care packages, don't expect elaborate replies to them, and let him make all the hard decisions for a couple more weeks. Then life, and your pursuit of clarity, can begin again.
posted by JimN2TAW at 6:54 PM on December 2, 2008

Joe is a sensitive guy, and he's probably wary about wanting to come on too strong, lest you think he's being a macho jerk-type, which us sensitive guys hate and would hate being.

You sound like you're doing everything right. Have you talked about sex with Joe, even in a joking way? If not, do so next time you go out. Bring up the subject first. It may not happen immediately, but Joe will see the green light and feel emboldened to get more physical. He doesn't want you to think him a macho asshole, but it's ok if he is, a little, at the right time.

And lastly, don't forget his schedule. First year at law school is notoriously demanding, and your relationship is long-distance on top of that, forging this relationship will be uphill, at least in those regards. You really need to be with a person consistently for it to work. But by all means go for it.
posted by zardoz at 8:47 PM on December 2, 2008

Basic advice: keep kissing him. It'll sort itself out one way or another.

Along the lines of what most folks are telling you, stay in touch, but don't make any demands on his time. robinpME's suggestion about how much contact seems pretty good, and just have those emails and texts be something he doesn't have to respond to at all. It should be fluff; nothing serious or thinky, just something funny you saw or heard or the like.

If he wants a study break, he'll call. Offer that you're available in the first message, and then let it drop. Chances are good that his brain is already a melange of contracts and torts and holy-crap-pretty-girl-and-kisses, and and I'm sure it's all shaky and exciting and scary and he's in a daze, and if he surfaces and wants a study break, he'll call you. Give him a good night kiss, and if he takes it further, that's just grand, and if he doesn't, that's fine, too.

I'll say this, though. Find him shortly after his last exam, and kiss the hell out of him. If he's anything like I was in law school, this will be the nicest thing anybody has ever done for him (in law school).
posted by averyoldworld at 8:19 AM on December 3, 2008

The first time I kissed my husband, he had never had a real girlfriend before and was too shocked to kiss me back. That went away after about a minute, but he tends to be a real "go for it" kind of guy. He was 18 at the time.

In other words, I could easily see a 25 year old guy in the same position, with a more timid personality, reacting how he did and being too scared to mess things up. I think it's kind of cute.
posted by Nattie at 11:39 PM on December 3, 2008

You are overthinking this. He clearly has taken the effort to spend money on you and spend his time with you. Time and money are valuable and he is giving both to you. This shows you he cares. He is not being affectionate because he is not used to it because, as you indicated, he has never had a girlfriend. He is unfamiliar with how physical to be with you. He doesn't know when it's too much or too little, so he defers to the safe-side. He thinks things through a lot, hence his interest in law school. Thinking vs. feeling. Get him used to feeling. That is all. Explain to him with words the level of touching you like. There is no right or wrong, just the touching-amounts that you each prefer. Please do not speculate the he is gay. He is dating a woman (you) and not another man. As to the other answerer whose gaydar "is going off the chart"... the guy asked for your number and took you on a date – most gay men do not do this.
posted by umlaut at 2:30 AM on December 5, 2008

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