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I feel like we're playing a game

I've known this guy for many years and he had a crush on me when we first met. He was the type who could charm any girl he wanted, but I was the first one who rejected him. He was overbearing and weird, and I wasn't looking for any kind of romance. I was too aware that we were just kids. After that harsh rejection we didn't talk until we met again in highschool. We had a lot of fun chatting as friends, then after a while he told me that his offer still stands and asked me if I was ready for a relationship. I wasn't, and I turned him down once again. It was the first time I've seen a weird sadness in him, but I don't regret my decision. A big reason why I rejected him a second time was because of his past. Everyone knew him as the school's biggest jerk.. what was I supposed to do? Every time I saw him he was with a different girl, and he wasn't able to hold a relationship longer than 3 months with any one of them. I'm still strangely disgusted by him because of that. I always refused to be just another girl he used to date and he's well aware of that.

I think the second rejection left a mark on him. When we randomly met again recently, he told me that he's been laying low for a year, trying to become more mature. He did seem more mature indeed. He wasn't overbearing, weird or disgusting to me anymore. We had fun talking to each other and I had a strange feeling of comfort while laughing with him about his college life and daily struggles as a young adult. He did make a few jokes about how spoiled I would've been if I was his girlfriend. He's always half serios half joking about me being with him. Then my friend (who was there to witness the whole thing) made jokes about how he's still in love with me, and how the chemistry is still there.. at least my friend had a blast laughing.

Then whatever that interaction was gave me so much to think about. We both grew up, and no matter how harshly I rejected him, he never stopped being sweet to me. That fun, comfort and safety comes with a lot of bad experiences from the past. Nowadays, guys are really pushy and rude if you're telling them no, they become your biggest enemy if you hurt their ego. This guy is different in that aspect. I can't believe that I kinda respect him now? Idk... I was also thinking about what a relationship with him could be for the first time in my life. Maybe the chemistry is still there, maybe I'd regret losing that connection if we never meet again in the future.
I was also thinking about how he managed to bring out a confident side of me. One thing my friends always told me was that I was abnormal for enjoying making the guy go crazy. I mean, I wouldn't dare to do that anymore, but I used to tease him and make fun of him every time we talked. I was always testing his limits when we were kids. I don't mean that in a weird way, I mean I was pissing him off in hopes of stopping him from flirting with me. The thing that shocked me the most was how he actually really liked that (as he told me a few years later).
He made fun of me later in life because I lost most of that childish confidence.

Whatever is going on between me and him always felt like a game. It's always fun but it never lasts. There's always something going on between us when we meet, but we only meet randomly. Nothing is ever planned because we don't text each other, we don't keep up with each other's lives. Somehow we just meet and talk as if we do that every other day. I don't know... I wrote all this despite being extremely embarrassed because I wanted to clear my head.. no matter how much I look at it, the whole thing seems like a story you'd find on wattpad. I want to keep having him in my life as a friend, but he's so stupid. Everything about him is stupid.. and everyone mistakes him for my boyfriend. I swear... I need to stop thinking about this.

 
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