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The original was posted on /r/tifu by /u/smallmexicanchihuaha on 2023-10-09 01:25:15.

A couple weeks ago I (28M) was by myself at a bar that I go to pretty regularly. I was sitting outside, just looking at my phone and texting some friends about upcoming plans when I overheard a woman who was around my age talking to some of her friends about how she had been single for a while and wanted to start dating again. This caught my attention and my first thought was “damn, I relate to that really hard,” because I’ve been single since before the pandemic. I guess I started eavesdropping because a few minutes later I literally heard her say “I kinda want to go ask that guy out.” I looked around and realized I was the only other person out there and honestly I found it a little exciting and flattering, but also knew she could have just been blowing off steam or something.

I thought about it for a little bit and I realized it might be a funny icebreaker to wait until she leaves and say something like “hey, you’re not going to ask me out?” But I also didn’t want to admit that I was eavesdropping or potentially put her on the spot and/or embarrass her in front of her friends, so I was debating it with myself. When she left we made eye contact and smiled at each other but I completely chickened out and didn’t say anything, and I’ve been regretting it because I don’t always have opportunities to meet people organically like that. I haven’t seen her there since, so I’m kicking myself and I really don’t want to fuck up my next opportunity to potentially go out with a cute girl.

TL;DR I overheard a cute girl at a bar say she was thinking about asking me out. Wanted to say something to her but didn’t, now I’ve been feeling like a lonely coward