So as most of your questions probably start out, I like this guy. Let’s call him Kyle. We are friends, but we aren’t entirely that close since we met only a couple months ago. How did we meet? Well my best friend dated his twin brother and then she broke up with him horribly. So, Kyle and I would chat over Facebook all the time, until I got his number and we started texting non-stop. I mean this guy actually stays up with my abnormal sleep patterns and will text me until 2:00-3:00 in the morning. Not to mention that even if we didn’t talk at all that day he will still send me a goodnight text, or good morning text.
At school he’ll always come and hang out with me for a while at lunch. Kyle also tends to comment on small things I do, for example; the other day I was reading and he just randomly says, “I like the way you push up your glasses” after me doing so. Kyle, knowing how much I like books, invited me to go with him to a bookstore and hang out and get coffee. Then last night he called me and asked if I was going to see the play he is in that day. I reply yes, and when I get there he kept telling me how much he was glad I came and hoped I had fun, etc. He is also extremely formal around me.
The only downside to all this that makes me doubt whether he is just EXTREMELY friendly, is that he has a girlfriend... He doesn’t talk about her much though, and when I see them together she seems kind of distant. Also, I haven’t told my best friend who dated Kyle’s brother, so I feel if I did things would get sticky. So Jono, what is your verdict?
Sparkler, this isn't even a Does He Like You post; it's a He Likes You So Now What post. The problem is, I didn't know Now What, so I consulted a LITERAL GIRL for her take on this situation, and this is what we came up with, with the combined wisdom of our many chromosomes.
Kyle does like you, but he has no idea what he intends to do with that information yet. He's in a relationship already. I mean, from how you've described him and his girlfriend, I imagine them doing only extremely unsexy things together (flying separate kites at opposite ends of a park, silently watching a whale have a baby), but they are still dating. He doesn't yet know if he wants to risk his actual relationship for a potential one.
Now, my first impulse was that you should pursue things with this guy anyway, but if you look at my past advice, I seem to think that everybody should immediately make out with everybody else as rapidly as possible. Tempered by some female tactfulness, my new advice is this: stay close with him, remain flirty enough that he knows you're interested, and leave the ball in his court. If he genuinely likes you, and his current relationship really is as unfulfilling as you suspect, he'll conclude that being with you is preferable to being with Completely Generic Girl. Three things have to happen before you two can get involved, though.
Both of you have to be serious about this.
Some people will say it's categorically wrong to disrupt a relationship, but if the dude barely likes the girl, and the girl barely likes the dude, and you and he are sexy bananas for each other, then why not pursue it? It is categorically wrong to engage in meaningless sexitude with a dude who's taken, of course, but if you two have genuine feelings for each other, I think you should both go for it. There's no reason he and his uneventful girlfriend should keep doing crossword puzzles together forever until the heat death of the universe. If he just happily continues to flirt with you but never makes a move, you may have to initiate this part by asking him what his intentions are; either way, you can't move forward until it's clear this is A Real Thing that is happening.
He needs to break up with his girlfriend.
This is the necessary next step if he is, in fact, interested in you. I have little experience with how this actually works. I've technically "stolen" a girl from her boyfriend before, but in that situation, she did all the hard work while I wandered around in the background going "HURR, WHAT I DO??" Then suddenly she was all "I broke up with my boyfriend," and, "Let's make out a bunch of times" and I furrowed my brow and was like "Waaiiit a minute... she may like me!"
The point of this story is not just to brag that I have had as many as one girlfriends. It's that, after she was reasonably sure I liked her back, she left the guy she was no longer interested in before pursuing anything with me. You have to expect Kyle to do the same thing.
You need to clear this with your BFF.
One final point that my female advisor reminded me of is that girls are not guys, which is a fact that I somehow forget. Your friend may harbor residual feelings that are more complicated than than a male worldview permits (a "male worldview" pretty much being "EAT HAMBURGERS, KISS A LADY.") I don't think this situation is all that tricky, since you want to date Kyle and not his brother. Of course, they are twins, so what if Bizarro Kyle shows up at your house wearing his brother's clothes and you accidentally marry him in a fit of passion?? (I don't think this situation is terribly likely, but I'm trying to allow that your friend might have reasons to feel uncomfortable about all this.)
The overarching point here is that I think you and Kyle are obviously into each other, but there are lots of third parties involved. If the two of you just start spontaneously making out from across the room, some toes will get stepped on, and also you will probably sprain something trying to make out at such a distance. I want to give you the go-ahead, but I think you need to proceed delicately, and make sure you've taken everybody else's feelings into account before you do.