F, late 20s, seeks Clueless for LTR leading to marriage.
October 13, 2006 2:27 AM   Subscribe

Since the whole bashing-on-head/dragging-back-to-cave routine is a bit passe, how do I go about getting the guy?

So, there's this guy. We've known each other since we were children and are very good friends. Right now he lives about 2000 miles away from me, but we catch up whenever we're in the same town, and talk on the phone or swap emails with some regularity. He's a great guy, we have similar family backgrounds and personal interests, our families like each other, etc. Left to his own devices, I'm not sure he'd ever get around to dating, much less getting married and having kids. Some girl's going to have to take the lead on dragging him to the altar if he's not going to end up a 50 year old bachelor. I'd like to be that girl.

I'm virtually certain that, if it were 50 years ago, our parents would have long-since arranged the marriage. My mom has been dropping hints about him since we were 18, and I know his dad likes me a lot -- and would like to see grandchildren before he dies. The last time I was at their house, he was actually directing the boy to sit closer to me, suggesting topics of conversation ("Tell her about [this foreign trip]"), etc. I think he knows (fears) that his son will never figure it out on his own.

So, absent old-school arranged marriage, what should I do? All the books and websites I can find that talk about "getting the guy" are talking about a guy, just any guy. I need tactics targeted to snagging the one in particular I want -- one who is self-described as "pretty oblivious to things like that" (ie, romance, flirting, hints).
Any success stories from similar situations would be more than welcome. I have no interest in tricking him into anything he doesn't want; I just think we could be very happy together, and need to figure out how to get him thinking along those lines too.

Worth noting: his sister and I are good friends as well. He's very socially isolated right now, works a lot at a lonely job, and doesn't have much contact with his friends. And he'd do almost anything to make his father happy.
posted by katemonster to Human Relations (59 answers total) 1 user marked this as a favorite
 
Er... ask him?

Failing that, I believe the modern equivalent to "hitting on head and dragging back to cave" involves multiple pints of stella.
posted by handee at 2:29 AM on October 13, 2006


A good friend? Next time you're back home, take him on a picnic/for a drink/walk on the beach/whatever and tell you have an enormous crush on him. For me, this might have been the ideal time for the boy next door to tell me he was gay, but it was the 80s. He just said that he didn't think it'd work out. The nice thing is my bud handled it so well, I didn't feel uncomfortable in his company.
posted by b33j at 2:40 AM on October 13, 2006


I agree with handee; your problem has a very easy solution. Tell him how you feel. Express your feelings explicitly in words ("I wanna be your girlfriend").
This will feel strange since 'normally' the prime directive with respect to these matters is to make maximal use of subliminal communication, hints, social cues, flirting etcetera.
Have fun!
posted by jouke at 2:42 AM on October 13, 2006


God yes, just take him out and tell him you fancy him. The whole marriage thing can come later.

If he doesn't get the message, snog him.
posted by chrismear at 2:43 AM on October 13, 2006


You could, as handee suggests, just straight up, ask him. Being straight forward, as a method, has a lot to recommend it, not the least of which is that it is the most unambiguous method.

But do it privately, so you've some sense of sussing out the situation in his head. If he's not into you, or not into girls, the effect to your life is the same, but far different to him, and to his family. What you learn, in fairness to all, unless it leads in the direction that caused you to post this question, should remain only known to you and he. It's entirely possible he'll deflect your questions entirely, even asked straight up. That's his right, and you've lost nothing, if he does.

At least, you'd know if it's worth while biding your time, any further.
posted by paulsc at 2:43 AM on October 13, 2006


I think it highly probable that besides being oblivious, your guy is also scared of the initial steps of establishing a relationship/ making affection known. I used to be this way. In fact, he might not be nearly as oblivious as you think. I could pick up on the cues quite easily, I just pretended to be dense so that I wouldn't have to enter uncharted territory.

Grab him and kiss him, at the most appropriate moment possible. A girl finally broke me out of it by doing exactly that. After that initial barrier was gone, I found that many things came naturally. Do something bold, don't dance around the issue, and if your guy likes you too he should be happy that you had the courage to take the lead.

Think of "bashing on the head" as "making your feelings known clearly." But do drag him back to your cave.
posted by Derive the Hamiltonian of... at 2:52 AM on October 13, 2006


You're 2000 miles away from him. Is that a good way to start a relationship? Just saying...

Also, does he like girls? Do you think he likes YOU?

However, once you two are closer together on a regular basis, just kiss him and announce that you two are dating now and if he doesn't like it, he can break up with you. If he DOES break up with you, say fine, and then go about your business.

Then, the next day, kiss him again and announce you're back together.

Repeat as many times as necessary 'till he gets the point.
posted by Brandon Blatcher at 3:41 AM on October 13, 2006 [1 favorite]


Wow, your suggestion sounds really creepy, Brandon. Announce that you're dating without discussing it? Announce that you're back together when he didn't want to be? Huh?
posted by grouse at 3:47 AM on October 13, 2006


Is he a virgin? If so, I would strongly suggest you give him a demo - he'll be yours forever.
posted by Meatbomb at 4:20 AM on October 13, 2006


Best answer: Yeah seriously, don't do what Brandon said, unless you're some kinda psycho.

Why don't you ask your parents to set you up?
posted by thirteenkiller at 4:28 AM on October 13, 2006


And here I thought it was humorous and charming among old friends and hit him over the head with what you wanted.

If it's too psycho, just sit him down and tell him what you want and see if he's keen on the idea.

If that's too blunt, then try explaining him to the thread, so people understand WHY he's obtuse these things.
posted by Brandon Blatcher at 4:38 AM on October 13, 2006


he's obtuse ABOUT these things.
posted by Brandon Blatcher at 4:40 AM on October 13, 2006


It all starts with a kiss.
posted by caddis at 5:04 AM on October 13, 2006


If I knew beyond a doubt the guy wasn't gay, I'd kiss him. If I had any doubt, I'd make a really funny joke, take his hand or rest slightly on his thigh, and then kiss him in the silence that followed.
posted by muddgirl at 5:12 AM on October 13, 2006


And here I thought it was humorous and charming among old friends and hit him over the head with what you wanted.

yeeah, but what about what he wants? it's entirely possible he has a different plan - maybe he's gay, maybe he wants to be a 50 yr old bachelor, maybe he's just not that into you, etc. So sure, you make it clear that you're interested when you have the chance, but in the modern world step 2 is up to him - these days marriages are only family affairs secondarily. Just because everyone around him would love this outcome, the primary question is whether the two individuals at the alter really want to be there or not.
posted by mdn at 5:16 AM on October 13, 2006


You should probably always do what the dinosaur tells you.
posted by electric_counterpoint at 5:20 AM on October 13, 2006


I find the best solution in these situations involves a puppet and ventriloquism.

Assuming your puppet is at the shop right now (whose isn't?), I agree with the others. Find the flimsiest excuse to kiss him and tell him you've been wanting to do that for a long time. Completely flattering.
posted by empyrean at 5:45 AM on October 13, 2006


Tell him what you want. Ask him what he wants. Find out if those things are compatible. This is someone who's not comfortable with games and intrigue, so skip those. Speak your mind clearly and kindly, avoid metaphor and allusion, and listen to his response. Putting yourself out there is hard and scary, but ultimately it is no more painful than years of beating around the bush.
posted by Lyn Never at 5:59 AM on October 13, 2006


fifthing the snogging.
posted by garfy3 at 6:01 AM on October 13, 2006


Oh, yeah, webcomics aside -- as a heterosexual dude, I would be flattered to have an admirer kiss me out of nowhere! At the very least, it would stun me enough that, if you slipped in a lightning-fast kiss-ask combo, I might agree to a date.

(Electric_counterpoint's lady admirers: TAKE NOTE!)
posted by electric_counterpoint at 6:05 AM on October 13, 2006


I'd advise against the snog. What if he is gay? If a girl I'd been friends with for years suddenly pashed me (er, back when I wasn't out, anyway), a very awkward silence would have ensued.

Talk. WTF is with people and not talking to each other?
posted by dirtynumbangelboy at 6:05 AM on October 13, 2006


How about telling him to read this URL:
http://ask.metafilter.com/mefi/48496 ? :)
posted by jozxyqk at 6:07 AM on October 13, 2006


I second the giving him a demo idea, as Meatbomb so eloquently put it.

The fastest way to a man's heart is NOT through the stomach, as some suggest.
posted by milarepa at 6:21 AM on October 13, 2006


If he is gay, I would suspect he'd be flattered (at least, I would be if I had such an encounter with a guy I hang out with, and heterophobia is not likely to be a problem, right) by the random kiss, if a bit surprised. And if he's hetero but not interested, again, I suspect he'd be flattered.

That said, I think the "hey, I like you. Do you think there's any spark here to work with?" conversation is your best bet.
posted by spaceman_spiff at 6:21 AM on October 13, 2006


I don't understand. First of all, you two live 2000 miles away. Not a good start to a relationship. Second, you're already thinking about marriage with this guy and you don't even know if he likes you like that. I assume the guy should have some say in his future. This is definitely leading to disappointment.
posted by Durin's Bane at 6:24 AM on October 13, 2006


Best answer: Are you able to use his sister to do some reconnaissance work for you? Nothing obvious, but perhaps a few subtle questions about how he feels about you (or dating in general) could give you an idea of where he stands.

And if indications are good, you could include some flirtatious remarks in your contact (which I assume include letters and emails). Let him know how much you're looking forward to seeing him again. Compliment him.

And then, yes, the snogging.
posted by suki at 6:29 AM on October 13, 2006 [1 favorite]


Yeah, y'know, not all guys are retards. When reading this, my thought was that he's probably sick of having his family try to set him up with you serrepticiously. A lot of internal eye-rolling etc., but he doesn't want to alienate you because you're friends with his whole damn family.

So, sure, tell him. Don't kiss him. Approach it like an adult.
posted by klangklangston at 6:31 AM on October 13, 2006


"Second, you're already thinking about marriage with this guy and you don't even know if he likes you like that."


Just a note: My wife felt that she would marry me after our first date. She didn't tell me that of course, and naturally, I didn't like her that much at first, but here we are, years later, all shacked and quite happy.

So, YEAH, it souds a little crazy, but love is a little crazy and things CAN happen. Go for it, just don't be TOO psycho about it. Realize that he may not want you.
posted by Brandon Blatcher at 6:40 AM on October 13, 2006


I was overseas and emailing with a long time friend. She had been married and I was friends with them both but they broke up while I was away. I suggested she come and visit me and she agreed. And then she wrote a message to say that her feelings for me were deeper than I had suspected.

We did meet up and things were hunky dory but the point I'm not making is, the email was really good for me, it gave me time, it saved me from embarrassing her or making an ass of myself. It gave me the time to check my own feelings and think about something that had not been in my head at all previously. If your boyo is a bit shy at all or given, as you suggest, to not knowing a romantic notion if it crashes into him, then write a gentle but straight forward email suggesting that it might be nice for you 2 to get together next time you are in the same town. It's less pressure --- whether he's gay, not into you or asexual --- he is your friend anyway, so he should treat you decently, even if he's going to decline the idea.
posted by peacay at 6:42 AM on October 13, 2006


Brandon: She probably felt that about every guy she had a crush on.
posted by thirteenkiller at 6:44 AM on October 13, 2006


thirteenkiller is right- If I was married to every guy I "knew" was The One, I'd have a billion husbands. On the upside, if and when I do get married, I'll be able to say, I always knew!
posted by ThePinkSuperhero at 6:58 AM on October 13, 2006 [1 favorite]


Thirteen, pink, if you're referring to my wife, you're incorrect.
posted by Brandon Blatcher at 7:14 AM on October 13, 2006


What are the odds he's content being single?

The last line bothers me, "And he'd do almost anything to make his father happy." I call BS on that. Sounds like this dude needs to grow up and get his own life.
posted by friarjohn at 7:14 AM on October 13, 2006


You may want to consider developing what's called a 'relationship.' In these 'relationships,' the intimacy between two people builds gradually, so that they learn to understand and trust each other more and more over time. Then, when a question about how to handle the next step comes up, they have a general idea of what to do, and that idea is based on actual experience dealing with the other person.

Here's a sample blueprint for dealing with this sanely:

Next time you're with him, kiss him (not on the cheek, etc.). Then, in the next email/phone call/whatever, tell him you had a good time and are excited to see him again, etc. If he sounds positive, take the kiss a little further next time. If that goes well, arrange for another visit in the near future, and take it further. If, after a series of visits that go very well, you are both feeling happy about the way things are progressing, tell him that you're thinking about moving to his city to be with him. Then do it. Then date for a while, while you're living in the same city. Then move in with him. Then, when that's been going well for a while, move on to the question of whether you actually need to get married, and if so how to go about it.
posted by bingo at 7:16 AM on October 13, 2006


Following up on what bingo said:

The simplest way to indicate that you want to be his girlfriend is to act like a girlfriend. Which means, you arrange time to be alone with him doing a date-type activity, then you act like you are on a date.

To spell this out, if you go to a movie (say) with a male friend to whom you are not romantically attracted, you behave like a buddy, right? You speak in a friendly tone, you maintain a "friend-appropriate" personal space. You ask your friend if he wants some of your Raisinets, then you pour some into his hand.

With this guy, your behavior is different: you speak in a quiet, intimate tone, you get close and you stay close. And you feed him the Raisinets by hand, one by one.

If he doesn't pick up on this quickly (e.g., within the hour) in anbvious way (e.g., trying to stick his tongue down your throat) then he's not into you, and you can drop it.

If he does pick up on it, then you continue in dating mode, including the kiss goodnight, and "I'd love to do this again. Would you like to call me?"

But to tell the truth, 2000 miles is a long way to go for a first date. Surely the earth is not completely scorched in your neck of the woods.
posted by La Cieca at 7:29 AM on October 13, 2006


I have read that for humans, being intimate (in a romantic way) with those you know from childhood, tends to be difficult. It becomes too much like being with a sibling. Be ready for this guy to really only think of you as a valued friend, and therefore, one with whom he can not be romantic.

OTOH, I do believe there are some guys that are utterly clueless about romance, and do need others to push them in the right direction.

Be careful you don't destroy a long-term friendship for the wrong reasons.
posted by Goofyy at 7:29 AM on October 13, 2006


If it weren't for the fact that your guy's father is still alive, and that my friend has already had this conversation with her guy, I'd swear that you were someone I knew. Anyway, here's what happened in my friend's case. She (leaving for LA) told her hometown best friend/boy next door that she had a little bit of a thing for him. He, while flattered, didn't do anything about it. The reason he gave was not wanting to hurt the friendship, but that's a pretty easy cover for a lot of different feelings, from "I'm gay" to "I'm just not that into you." So I wouldn't hold out much hope. Chances are that this guy has already considered a relationship with you and decided against it for whatever reason. But you'll never know until you ask, so isn't the first step kind of obvious?
posted by MsMolly at 7:30 AM on October 13, 2006


I am a man that's equally dense. I've even had someone make the first physical move, and only found out about it too late ("oh, you mean that was why she kissed me?"). On several occasions, now that I look back on it, I've had women hitting on me without even the tiniest bit of awareness on my part.

I regret my failure to react during all of those events, because I was actually interested in all of those women. Really. I actually am that stupid, if you can believe it.

My "reasons" for being so dense may not be his, so I'm not going to waste your time discussing WHY he might be so dense. Instead, I'm just going to explain what would work, if he's as dense as I am.

I think you need to be blunt. Really blunt. Kissing him is not sufficiently blunt. Sit down at dinner sometime, and simply say it flat out: I'm romantically interested in you, would you be willing to try a romantic relationship with me?

Look, you don't want to spend your life wondering what-if. I've had this exact same chat with a woman that said no to me, and we're still extraordinarily good friends, so it doesn't have to be a one-way ticket to losing him.

If you end up regretting something, it's better to regret the choices you made rather than the choices you never had the chance to make.
posted by aramaic at 7:39 AM on October 13, 2006


I came in to say exactly what Goofyy said -- the romance thing just feels oddly incestuous with childhood friends, and he might not be comfortable with it. That's not to say you shouldn't try, of course; if you like him, you should tell him. But it's a possible explanation for his apparent obliviousness.
posted by danb at 7:40 AM on October 13, 2006


I think kissing him might be a bit too foward. Just tell him exactly how you feel, and see what happens.
posted by chunking express at 8:09 AM on October 13, 2006


I'm like aramaic. (Well, I used to be. One of the benefits of getting older is that I can hear the cluephone on the first or second ring.) Suffice it to say that when I was in my 20s, a girl pretty much had to hit me over the head. With a neon sign. If this guy is like that, act accordingly.
posted by adamrice at 8:24 AM on October 13, 2006


Get him drunk and kiss him.
posted by beachhead2 at 8:33 AM on October 13, 2006


i agree with telling him bluntly. leave no room for confusion.
doing it over email could be problematic. i know i tried something similar with my current boyfriend, and the days it took him to formulate a response were really terrible. i had no idea how he felt and the fact that he freaked out and stopped talking to me for a week only made it worse. in the end, it all worked out fine- i called an appologized for sending the email, he called me back, we hung out, andi guess started dating within a week. that was a while ago though.
posted by kendrak at 8:46 AM on October 13, 2006


I think the important thing is too get him in person and just lay it out that you have romantic feelings for him. Dont just kiss the guy, you need to let him toss around the idea in his head before you throw yourself on him, not to mention if he does have those feelings for you then do you really want to cheat yourself out of that wonderful new relationship first kiss that comes at the right moment?

If he isnt interested, or acts overly akward to a point that concerns you make it very clear that the friendship is more important to you. it is 100% in yours and his power to not let akwardness ruin a life long friendship.

If hes not interested let go and leave yourself open for the person that really will make you happy.
posted by trishthedish at 9:23 AM on October 13, 2006


If you really have to pursue this guy, one "trick" few guys can resist is when a gal mentions how much she enjoys performing fellatio. He'll be much more receptive to talking after you show him you mean it. (Sorry O my fellow men about spilling our Big Secret, but it IS true, n'est-ce pas?) Until then, well, good luck sparking his interest; just stay in touch until you can arrange a meeting, at which, over drinks, you confide....
posted by davy at 10:03 AM on October 13, 2006


A couple more things:
1. Don't do it by email, it is very impersonal. You should talk face to face.
2. Don't mention blowjobs.
posted by chunking express at 10:20 AM on October 13, 2006


Well, I'm probably clueless enough to comment.

First, I think the surprise kiss is an absolutely terrible idea. The shock value of it is likely to totally freak him out, even if he is attracted to you: it's not going to give you an instant idea of how he feels. Plus if he's very inexperienced he might be unsure of the basic etiquette and mechanics of it, which is only going to make him nervous.

Second, be very prepared for rejection. If he's known you for so long without ever trying anything, it seems highly likely that he's not interested. As others have said, he may be committed to being single, he may think of you as a sister, he may have his own "type" that you don't match.

Just tell him outright, honestly and face to face that you're attracted to him, preferably in a low-key manner, and see how he reacts.
posted by TheophileEscargot at 11:21 AM on October 13, 2006


Just get in there with it. It's not like you have a lot of competition. He sounds a little shy, so don't freak him out, but being direct is really the best go of it, I think
posted by GilloD at 11:31 AM on October 13, 2006


Best answer: I'm with beachead2. Had a good friend for 12 years - worked at the same music store, did some musical projects together, lots of common interests. We both saw each other go through several disastrous relationships. Always thought this person and I would be perfect for each other, but there wasn't a "spark" I thought, and the timing was never right. Then one night we met at a party for the old music store neither of us worked at anymore. He'd just got back from a tour and we got to talking again. Let's just say he had the jet lag and I had the chardonnay. Bitchin' hangover the next day, but it's three years later and we've been very happy together!
posted by Wylie Kyoto at 11:35 AM on October 13, 2006


Response by poster: All right, a little more information, for anyone still paying attention (I 've been in a place that allegedly had wifi, but nobody could get an IP address).

More about him: he's very much the absent-minded professor type. He's been so sunk into school/work for years that he doesn't make time for much of any kind of social life. He has always had to be dragged out of the house to go do things, which he then enjoys thoroughly and is reluctant to go home. To my knowledge, he's basically never gone on a date. I honestly think he's one of those guys who just hasn't gotten around to it yet (the ultimate late-bloomer) and won't think of it on his own until many years from now. If I'm wrong, I'm wrong. I'm a big girl, and I'm willing to deal with that. And if he's content being single? Great. Fine for him. Like I said in the OP, I don't want to trick him into anything he'll be unhappy with. This is not about me getting my way, regardless of his feelings. It's about approaching him in the best way to make this work, if and only if he's amenable to it.
Bingo, thanks for the tutorial on what a relationship is.

Something that I think I did not make sufficiently clear in my post is that, if arranged marriage were an option, I'd be totally down with that. I don't want to date him for dating's sake, I definitely don't want to move in with him, and I'm very goal-oriented on this. Based on what I know of him up to now, I think we'd suit each other very well. Plus I think he's absolutely adorable. Call me unromantic or overly pragmatic if you will, but several of the longest-lasting (over 50 years) and happiest marriages I know started in precisely this way.
As far as pleasing his father goes: his family is very important to him. That's one of the things I find so attractive. My family is very important to me, as well. He and I are ethnically similar, and our cultural values involve a closeness and respect for family members' opinions. I certainly wouldn't marry someone just to make my parents happy, and I would be shocked if he would; but knowing how much they like him would be icing on the cake.
I'm marking a few as best, but still welcome more input (especially elaboration on the themes).
posted by katemonster at 1:01 PM on October 13, 2006


More about him: he's very much the absent-minded professor type. He's been so sunk into school/work for years that he doesn't make time for much of any kind of social life.

This sounds a lot like me (hopefully in the past), so I reiterate my suggestion of being extremely blunt and open with him.

I must say, however, that your focus on marriage seems to be overwhelming your interest in the person. In other words, you've chosen this guy because he's convenient, not for his intrinsic qualities. His character/personality/attractiveness etc., may be all well and good, but it's sounding to me like they're entirely secondary concerns (putting it more cruelly, it's like you're looking for a Marriage Object, not a person).

Hey, I could easily be wrong, but I think it's a very serious possibility. Speaking purely for myself, finding out someone married me just because I was convenient & agreeable would destroy me. Then again, I appear to have a different cultural background, so FWIW.
posted by aramaic at 1:23 PM on October 13, 2006


Response by poster: Aramaic, I think you do have a point there. I don't *think* that's what I'm doing, choosing him just as a marriage object -- there are easier targets I would have chosen if that's all I wanted -- but I can see how it would appear that way.
I try to be cautious about how I think of him, and not just assume he'll conform to my every view of how things should be. There are things I know about him and his character from our years of friendship, but I don't know how they would play in a romantic relationship.
I'm not looking to call him up tomorrow and set a date for the wedding; what I want is more along the lines of an old-fashioned (very old-fashioned -- like Jane Austen) courtship where we both know what this is heading towards, and we spend some time finding out if this will work for us.
To put it another way: I already know I love the boy. I also know I am attracted to him. I would love for him to reciprocate, but I would rather get an outright no and recover from that than have several months or longer of aimless dating that fizzles out. If he's not interested in seeing if marriage might be an option, then I don't want to date him at all; I'd rather keep our friendship the way it is.

Am I making sense?
posted by katemonster at 1:57 PM on October 13, 2006


Hey, katemonster; you're right, family is VERY imporant! (If you love your own family, anyway.) It's all cool to say "I'll love him anyway, despite my friends and family think he's a jerk," but in the long run nobody's gonna be happy. My family and best friend just love my SO. And I'd love him anyway but this is SUCH a plus. Do something about the 2,000 mile distance and go for it! Love is the best thing in the world.
posted by Wylie Kyoto at 2:04 PM on October 13, 2006


Aha, I think I see what you mean.

OK then, if you choose to have the blunt conversation, you should add in a line about looking for a "serious" romantic relationship with him rather than just a fling or a casual dating arrangement.

...most folks I know (small sample, mind) would understand immediately what was being said, without the potential panic-inducing aspects of "hi, my goal is to end up marrying you".

Um, you may have to give him a bit of time to mull things over, since this conversation is more complex than a simple "I'm attracted to you, are you attracted to me?" chat. He may need some time to figure out what he actually feels (I would have, anyway). Speaking purely for myself, my reaction would have been first to be stunned, then to think "woohoo, someone likes me!" and only then would I be able to think clearly about it.

One approach would be to explain yourself ("I want a serious relationship with you"), get an initial reaction from him and then give him some time & space ("this has probably been a bit of a surprise, so you don't need to give me your thoughts right now").

You certainly don't to catch him in the initial "woohoo!" stage, only to later find him reconsidering his initial enthusiasm. Especially since it's such a short step from excitement to panic (and vice-versa).

...again of course, that's just me.
posted by aramaic at 2:14 PM on October 13, 2006


Also, I'm a giant giant nerd, but when I was in your position, I actually scripted out my "speech" and wrote myself some reminder notes I could refer to during it. Mostly because I was terrified of saying the wrong thing in my state of near-panic.

Even though the answer I got was No, I think the notes helped me make sure I framed things in a way that didn't damage a very valuable friendship.
posted by aramaic at 2:18 PM on October 13, 2006


his sister and I are good friends as well.

If that's the case, I don't understand why you're asking us, who don't know anyone involved, rather than the sister, who knows both of you very well. Have you really never said to her "I'm nuts about your brother, do you think I have a chance?" If so, what did she say? Surely she has an inkling as to whether he's interested in you.
posted by languagehat at 2:22 PM on October 13, 2006


As a counterpoint to the comments from Goofyy and danb regarding dating someone you’ve known from childhood.

I’m currently dating my college roommates 7 year old sister (Relax, 7 years old 28 years ago. We are 35 and 46 now.). I think I’ve known her since she was 5 and I was 16. There were times when it felt a bit weird at first but that soon passed.
posted by Carbolic at 2:40 PM on October 13, 2006


Why not watch "When Harry Met Sally" together?
posted by davy at 4:21 PM on October 13, 2006


hmmm. I need to read these questions better. I missed the part about the sister until I read languagehat's comment. That is the ticket. Tell his sister you like him romantically but don't know how to tell him. She will take care of the rest. Without the sister I think finding a nice romantic situation to keep some romantic eye contact and then a kiss would catch the shy guy who is interested every time. If he doesn't take the hint from his sister a kiss might still convince him anyway. You have options. Good luck getting your guy.
posted by caddis at 7:49 PM on October 13, 2006


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