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I've been friends with this one guy (let's call him "Jack") since I was little. I started liking him as more than just friends when I was in eighth grade, but I didn't tell him how I felt until I was a sophomore in high school. He told me that he didn't feel the same way and that he didn't want a girlfriend at the time. I spent the next few years trying to rid myself of my feelings for him.
Now, we're both a few years into college, and I'm starting to fall for him all over again. The most recent time we hung out, he paid for everything we did, but I'm not sure if he was just doing this as a kind gesture or if it was a date. He has lots of friends who are girls, and I'm not quite sure where I stand! – Confused at Central Michigan
A lot of guys have gotten used to having to paying for everything (or at least offering to) when going out with a woman, regardless of whether or not there are romantic implications at all. Many of us are taught that paying for everything is chivalrous.
I’ve been in a situation not too different from yours. I met a girl in high school, and for years we were the school’s “will-they-won’t-they” duo. We went through periods of liking each other to actually and actively disliking each other, but we never actually dated because I could never get a proper read on her feelings (and I never got the guts to man up and ask her out, but that’s an issue for another article). Ultimately, this led to my decision to completely ignore her for a year after we graduated just so I could get rid of my feelings for her. It worked, and we have since resumed communication and are now better friends than before.
Even still, whenever we meet up at Starbucks, I almost always ask her if she wants something, even though I know she’ll turn me down. I don’t do this because I still have feelings for her; I do it because I was taught that when you go somewhere with someone, you offer to get something for that person. But this lesson goes for any of my friends (guys included), not just people I’m romantically interested in.
So unfortunately, Confused, I don’t think that his paying for everything means that he wants to start dating you. That said, a lot of time has passed between high school and now, so it’s entirely possible that he realized he does have feelings for you. I don’t want you to get your hopes up, though. Just because it’s a possibility doesn’t mean it’s a probability. You did say that he has lots of friends who are girls, after all.
Where do you go from here? Ask him if he wants to go out again. Call it “hanging out,” or call it an actual date, but see how he responds if he says yes. An enthusiastic agreement might mean you finally have a shot, whereas an answer like “let me check my schedule” (or something equally as apathetic) might mean that he’s just looking to be friends.
Be proactive. Take the bull by the horns and make an effort to really find out where you stand.