So, I dated my high school sweetheart for three years. We grew though, and he ended up being not at all interested in me romantically or sexually, so we broke up. Well... we broke up six months ago... and then tried to patch things up a month later... and then two weeks ago we decided to just let it go and just be friends. And adapting from a relationship to friendship hasn't been too hard for us. Honestly, that was just natural. I had pretty much lost all feelings for him six months ago. So, despite being on a break for six months, most people think we just broke up. Really, we just decided not to try and fix anything anymore. He's moved on, I've moved on. Well, about three months ago I started feeling really guilty because, lo and behold, I started crushing on a friend. Crushes are a really rare thing for me. As in I've had two ever. I've dated guys to fit in, or just because it seemed logical, but crushes? It'd be down to my recent ex, and this girl. We're very close, despite the fact that we don't get to see each other in person often. We talk every day, text for most of it, and even video skype when we get the chance. Honestly I'm so head over heels for her it's crazy. And she's not straight. And there was a time recently (and most of the time I still think this) where I would swear she had a crush on me. And this isn't just a recent thing. We've been this close for well over a year- and it shows no signs of weaning. I'm pretty sure she flirts with me a lot, I just don't know if it's something she does with a lot of people. A mutual friend noticed it, and made a lot of jokes about "being a third wheel" last time we all hung out. She's constantly complimenting me, replying to pictures of me with "be still my gay heart" or other variations. We found each other on a dating website a few months ago "just because" and she's constantly bringing up/joking about the fact that we're 97% matched. I don't want her to think I'm someone who jumps from one relationship to the next, because liking her as much as I do is so rare for me. It's also complicated because of the distance. The next time I get to see her in person is in about two months. I'm wondering if I should wait some time to talk to her about it until after we see each other, or before. Or anytime soon. If she is interested in me, I don't want her to think I'm not and miss my window. Is any of this even a good idea?
If you really like her, tell her, because she seems to be making the same sort of gestures to you. It's easy to overthink things and tip toe around on those eggshells for fear of breaking them, but you are now free and single and can afford to take a few chances and hopefully reap the rewards. I'm not suggesting you overdo it to the extent that you scare her off, but now that you have already met and built up a rapport there is no need to keep playing it really cool either. If you are honest about the fact that you like her it could move things along on your next date together. Are you taking a bit of a gamble? Yes, you are, but that's true of almost every relationship. Are there issues relating to distance? Yes, but if you are both serious about making it work, you will find a way.
Thanks for the responses guys! I'm on the fence, and it might be my low self-esteem, but I digress. I will be positive that she's interested, and flirting with me, but then I'll just wave it away as wishful thinking. Or I'll just keep seeing signs that she's flirting, and then when I'm trying to think of evidence, everything suddenly seems innocuous and innocent. I'm less scared to get hurt than I am making her uncomfortable or something, but the risk is worth it in my opinion. It'd be helpful if I got to see how she interacted with other people, but the only mutual friend we have is one I introduced to her just a few months ago so she's not that close to them. I talked to her the other day about my last relationship, and she's totally aware that it ended a long time before it officially ended, and in fact reassured me that it wasn't selfish of me to already be ready to move on, so I'm no longer concerned about that. So you think I shouldn't wait? The only reason I'm thinking about waiting is because when we see each other it's so rare. I see her in October, and then won't get to see her again around another six months, when she visits. I don't want to put a sour note on the trip. (On that note, I just remembered that she talked about having a real need to be affectionate with me and how she would probably want to spoon with me a lot when I visit, and that's a little affectionate and flirty even for us).
