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The original was posted on /r/tifu by /u/According-Tea-3014 on 2023-08-08 23:50:21.

So this happened back in highschool, but sometimes I think back and I cringe real hard at myself because I have to be the densest mother fucker.

So, I used to have a huge crush on this girl I went to school with. Like a massive crush, like a two-year long crush. She was basically my best friend, we always hung out together, usually in our group of friends. We talked anime, and just a bunch of nerdy stuff. The first year I was crushing on her, it took a while to build up the courage to ask her out (self esteem has always been non-existant), and when I did she said no. Disappointed, but I still wanted to be her friend so we laughed it off and moved on. We ended up hanging out A LOT more after though. Not a whole lot outside of school, as her dad was fairly strict and protective (for reasons, not just being controlling or anything like that). But still, it was nice seeing her more than I already had been.

The second year, our mutual friends had essentially cornered me, telling me I NEEDED to ask her out again because she had told them that if I had asked again, she would say yes. They were her best friends since like elementary school and I didn’t think that this would be something they’d lie to me about, so I decided that I’d ask her out again. It only took about a month for me to get the courage to do so. And she said no. Again. This time I WANTED to be frustrated, but there were some things in her background that were at play and I just couldn’t be mad. So I wanted to still be friends. Again.

Now this time around, not only did we end up spending EVEN MORE time together, she started opening up a lot more about her personal life. Which felt really nice to be trusted. A few months go by and her friends tell me AGAIN that I NEEDED to ask her out. This time, I just couldn’t, I told them that it was clear she wasn’t interested and that I was just going to be her friend. They argued, but I wasn’t going to change my mind. And throughout that month, she would bring up subjects that we had never rwlly talked about, like sex. To the point she was telling me that she REALLY wanted to try oral. And I mean, she’d bring it up almost every time we hung out. And by this time, my self-esteem was non-existant (more than it was any way) so I just assumed that she was over sharing.

Toward the end of the school year I was told that we were moving to another part of the state, and I was upset, but it was whatever. Next day, her and I are walking home from school and she had asked her other friends to let us walk alone. Didn’t think anything of it, until she started talking about how she was sorry for rejecting me, and that she felt like she had been dropping a lot of hints. Now, I was confused. I wasn’t putting anything together and I think she knew that because after a moment she asked me out.

To say that I felt HORRIBLE for having to turn her down because of the upcoming move is an understatement. Up to this point I’ve never had to reject anyone and I haven’t sense and my God it sucked.

TL;DR self-esteemed my way out of a relationship with someone I was chasing for two years.