How can I get a conversation with this girl I like?

Walk up to her and say “hi.” Then ask if she’d like to hang out some time. If she says yes, make a suggestion (such as going to a movie). Have a second suggestion ready just in case she doesn’t seem keen on the first one. Maybe there’s a musical performance the two of you could go to (a local band, an open mic night, whatever). If one of those two options sounds good, set a time and place to meet (you might want to figure out in advance how you can get the two of you wherever you’ll need to go). Exchange phone numbers just in case something comes up (offer yours first). If you say something awkward, laugh it off and be honest: “Sorry, I’m trying to act like I’m not nervous and failing. Let me try again.” If she is interested in you, she’ll be nervous too—and likely to forgive you for messing up a little as long as you don’t get bent out of shape over it.

One other thing: women are not another species; they’re human beings. There’s no “special” way of talking to them. Don’t try to figure out what she wants to hear or what kinds of “tricks” will get her to like you. Treat her like you would anyone else, except nicer (because you like her, so you shouldn’t pick on her the way you might with some of your male friends).

Ask her to go for either coffee or a soda. Ask her questions about her music. Then talk about yours. Then move the conversation to movies.

Look at this way: nothing bad will happen if you try to talk to her, but something bad will if you just skip it.

If you have a pretty good idea of where she might be on campus, during class breaks, at lunch or whatever, or if you know where she might hang out after school, whether it’s the dance auditorium or wherever, you can plan to be there and then you can simply go up to her and say, “Hi, my name is jonbanksrules. I’ve been seeing you around a lot and I thought now was as good a time as any to introduce myself. I think we have a few friends in common too. Do you know Meagan or Rick?” She might be nervous too and just say, “Hi jonbanksrules” and forget to introduce herself. If you know her name, then say, “Your name is Karen, right?” or if you don’t know her name, say, “I’m so sorry, I forgot to ask you your name.”

It might be best if you could conspire ahead of time with either some of yours or her friends (since they all seem to like you and think that she might be interested in you) to have a plan to meet at Starbucks. She might feel less awkward if you asked her if she’d like to meet up with you and a few other people. If she says she can’t go on that day, then ask, “Well maybe we can get some coffee on another day, if you want to.” Her answer to that will let you know if she really is interested in you or not.

She’ll either agree to go with you and the group, or she’ll suggest a different day, or she’ll hem and haw and not give you an answer (basically that’s a no, without having to hurt your feelings or be impolite).

If she gives you definitive answers (she says yes, or suggests another specific day) then it’s pretty clear that she likes you.

If she says yes, to the group thing or an individual thing on another day, don’t just walk away. Say something like, “I heard you play guitar, that’s really cool because I love ____ fill in the blank guitar player. When did you learn to play? Oh yeah, I have a ____ fill in the blank guitar, but I’m not very good at it, maybe you could give me some pointers.” Or if you are good at guitar playing, say, “Maybe we could get together in the lunch yard and do some duets.”

If she hems and haws or is too open ended or has some unusual or cliched reasons for why she can’t visit with you, it’s likely that she isn’t interested in you, only likes you as a potential friend, has another boy that she likes, or is heavily restricted by her parents.

If she seems interested, then say, “Maybe I could text you. We could talk about guitars and stuff.” She’ll either give you her number, or come up with a reason for why she can’t give you her number.

Then, if she gives you her number, don’t play games (like older, but less mature men do) by waiting around to text her. When you get home from school that day, give her a short sweet text that says something like, “Hi Karen, it was nice to formally meet you today. Looking forward to having coffee on Tuesday : )” Then take it from there.

I wish you the best of luck.

Ice-breaker: ask her opinion about something she is well-versed in.

Just walk up to her, grab her lapels in both hands, and say I’m so fucking crazy about you. Then smile and step back.

Welcome to Fluther.

Well, you’ve already told us that you’re too shy to talk to girls, or this one, anyway, so all the well-meaning advice about how to do that is probably lost on you, isn’t it? For that reason I like @Adirondackwannabe‘s advice for its sheer audacity, but it still involves talking to her, however briefly, which I suspect would be a greater problem for you than grabbing her by the lapels. In any case, grabbing a young woman “by the lapels” is such a high-risk activity, because it can be misperceived by everyone around, including the object of your affection, and worse, your hand could slip, and then the perception would be that you were a lunatic trying to grope her breast. You’d never be able to talk to a young woman at that school again.

So as much as I admire the chutzpah of the advice, I cannot recommend it.

But others seem to have missed a crucial element of your narrative: You say that she’s out of your league and you probably don’t deserve her. Bullshit.

That’s key. You’ve already proven yourself to be at least intelligent enough to pose this question and describe it in Standard English using good writing skills, vocabulary, spelling and grammar. (It could be better, but it gets the point across and is much better than a lot of high school writing that appears here.) So you’re a reasonably bright guy. You seem to be personable, self-aware and sensitive, so you’re not some creepy ogre (unless you’re very skilled at dissembling and hiding who you really are, but those people seem to have very little trouble acting and manipulating people, so I don’t think you’re that guy). You seem to be appreciative of her for many other qualities than just her looks, so you’ve got that going for you.

So I’m going to go out on a limb here and say that you have a problem that you need to address, and a girlfriend at this time is going to cause you more problems than it resolves. Because as long as you think that she’s “out of your league” – she will be. That’s a certainty.

What needs to happen – to you, in your life, or even just in your head – for you to believe that “your league” is much wider than you currently believe it to be? How are you going to “up your league” – or at least more accurately perceive what your league already is – to at least feel that you have a chance with her, before you even start this conversation?

You need to resolve this, because even if the conversation were to magically start tomorrow, and you found all kinds of interesting things to talk about and were simpatico in areas you haven’t even realized yet, if you feel undeserving and out of her league, then she’d have to spend too much time and effort trying to convince you otherwise, and she would soon tire of that and make your prophecy self-fulfilling by dumping you.

So you need to start with your professed feelings of inferiority. Once that’s handled, the conversation will come more naturally.