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Is there a chance for us? What do I do?

Tagged as: Friends, Teenage<< Previous question   Next question >>
Question - (22 May 2011) 1 Answers - (Newest, 28 September 2011)
A female United States age 30-35, anonymous writes:

There's this guy I've been interested in for, well, basically my whole life, but it's really quite complicated. Let's call him Tim.

We were best friends in elementary school and had crushes on each other off and on for like, 3rd-5th grade. Neither one of us really ever did anything about it, but there was definitely something there. Mostly, Tim and I were just really good friends.

In middle school, we lost touch due to differing schedules.

In high school, our classes intertwined again. But now we weren't friends anymore since we became friends with different crowds in middle school. In 10th grade, a mutual friend who wanted some people to be in her homecoming group set Tim and I up since neither of us had dates. We went as friends, obviously, and it was really fun. After homecoming, our group got really close and started hanging out all the time. I started to like him again, and he was flirty back.

Then, out of what seemed like nowhere, Tim asked out some other girl. This wasn't just any girl though, it was a girl that I've hated since middle school, and she's hated me too. We're really similar (in looks, smarts, athletics, confidence) except for the fact that she's a super aggressive b*tch. She's always had it out for me (I promise you I am NOT paranoid-- other people have noticed her malovalence), and I think when she saw me and this guy flirting, she saw what a great catch he was and decided to "steal" him. Well, her super aggressiveness in flirting pushed me out of the picture and won Tim's heart, since it turns out he had liked her in middle school and, now that he had the opportunity, he wanted to go out with her. They dated for almost 8 months. It was a terrible time for me. Our group of friends got into some fight and was torn apart. Tim and I stopped hanging out altogether, and I grew into hating the both of them.

Eventually, they broke up for reasons I'm unaware of. I like to think he realized she's a b*tch. One of our mutual friends told me recently that he thinks the whole relationship was a mistake, and he actually did realize how mean and selfish she was. Tim and I still didn't talk after that until very recently. I've had a couple of things with different guys this year, one of them being a good friend of Tims, but I've ended up breaking them all off early, before the relationships even began, because I realized I was comparing them all to Tim.

Tim is starting to get friendlier with me. Not super flirty, just 80% friendly and maybe 20% flirty. It's really weird though, because I thought we weren't friends. You see, Tim is still good friends with his ex (the one who hates me and I hate) and I figure he would know that I can't stand any of her friends. But he's acting as if we are friends. And there are times when he flirts, not a lot, but just simple teasing and the like. In the halls over the past couple of weeks, I've caught him glancing at me, which I don't remember noticing before.

I had a long talk about this with my best friend last night. I think I don't necessarily have a crush on him, but I do want us to be boyfriend/girlfriend or at least hang out more so maybe he can get the chance to develop similar feelings for me. I don't get nervous around him or anything, I just really like when he's around. Talking about him so much last night though made him enter my dreams. In my dream, my parents wanted me to kiss a stranger. Tim was standing next to the stranger, and we shared a look and kissed eachother instead. Then we ran away together.

So. There's the situation. I know when I go back to school, he's still going to be hanging out with his ex, which will make me upset. My question is: should I pursue this? My friends know all about this, and when a different one hears it all for the first time, all they say is, "Wow, you and Tim are like perfect for each other now that I think about it." I think so too, and I wonder if Tim is on the verge of realizing the same. Maybe he already has though, and he's just as lost as I am. Or maybe he's moved on completely, and the small signals I'm picking up on are actually nothing. What oh what do I do?

View related questions: best friend, broke up, confidence, crush, flirt, his ex, teasing

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A male reader, notanemo United States +, writes (28 September 2011):

Wow if you spend that much time typing you must love him i mean wow i think it would be a terrible mistake not to date him. but slowly slip it in so that you dont look despereate but if u do hes ur friend and will get over it

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