Kilroy stumbles around, is probably in love
 

Well, I guess a little history is in order.
I've never had a girlfriend. Yes, it's as pathetic as it sounds. Half the time my friends have had heart aches, I've wondered what the point was. I haven't actually had any thoughts about 'dating' or anything else, except for the natural teenage hormone induced dreams.

Now, at high school I got to know this cute girl. After high school we stayed in contact, mostly via email. We've been at the movies several times and I actually thought I knew her pretty well. I've actually wondered if I were in love with her. And how to tell her so. I hadn't though, because I wouldn't destroy the friendship-thing we had. Hell, she's fun and intelligent to watch movies with, and to destroy it with a bad comment? Well...

So today I wrote her a email, asking her about things. Apropos nothing at all, she said she had been seeing some guy since february and that "it's probably over now" and then she continues with the usual update about how her life's been shaping up. University, her appartment, that sort of thing.

I feel... confused by this. First of all because I thought I knew her, and that she was having a boyfriend... Well, I get jaloux. And disappointed, perhaps, because I didn't know and haboured these thoughts. Second, I started thinking the obvious "I might have a chance".

So... anyone got a piece of advice?

I can see if you're unsure of what she feels about you, but all you can do is ask her. Or you could just tell her about your own feelings first (I'd say it feels more appropriate to do so). If you got along with her well chances are that she does like you more or less and could consider you as a boyfriend. It could be hard if you're too far into the dreaded "friend-zone" though, but you shouldn't be worrying about that. If you just relax and don't make too much of a deal about it she'll most likely stay friends with you even if the answer is no.

Advice? Don't turn it into a game. You know her and you care about her, so tell her. Either she'll embrace it and you'll fly off to Pleasure-Town together or you'll find just how heart ache feels. That, or you can stay quiet and let your feelings simmer while some other guy with bigger balls takes her home.

Regardless, if you think that you might be in love, you're not. Love's about as subtle as a brick to the small of your back, or LeHah.

If you're not in love with her but still want to date her, then ask her out. It sort of sounds like you think the only point of dating is when you're head over heels, and it really isn't like that.

At your point, there's no way you can be in love with her after a few movie dates and email conversations. You're probably infatuated. The best time to tell someone that you love them is after you've been seeing them for a while, in my opinion. Enough to be sure that she loves you too or you would scare her off.

That's just a side issue. The real issue is what to do now. I say go ahead and ask her out again. She's single and ready to mingle, it seems. Take it slow. Yeah so she dated in Feb. Hopefully not too shaken up by the loss of the relationship, which was short term to begin with. Don't worry too much about the boyfriend. Couldn't have lasted more than a couple months.

I think you should just do it, lest you regret not acting later on.

I personally stick with the carpe diem option; you may as well tell her and see how things go than spend years being "friends" and hating how you can't be with her. At least if you get a firm rejection you know where you stand. Not knowing is more painful.

I've been here before... The whole "finding out second-hand" that a girl you like is seeing someone is a real weird feeling. Did you feel your stomach kinda knot up? That's the feeling of "ouch, I guess I don't have a shot, and didn't have a shot." The worst is finding out when you see them start to make out. Yeesh...

Regardless, don't make the same mistake I did and not tell the girl. Tell her. And don't half ass it with the feelings. Tell it like it is. Just do it. The worst thing that can happen is that she'll say no, and you'll feel some heartache. Letting your feelings boil inside you is the worst thing, this I promise you.

And yeah, what Frank said... You'll know it when you're in love, brother.