Following up from a post in a separate thread (The stories you tell! - Miscellaneous and Personal Stuff I Must Share - Straight Dope Message Board), I thought I’d like to know what things people regret the most…
For my part, there are two things:
The first occasion occurred when I was in college (in 1990). I had a huge crush on a girl (who I will call Sarah, for the sake of this post) who was, if truth be told, WAY out of my league - she hung out with all the jocks and I was…well…not a jock. She was really cute and there were lots of guys who had the hots for her. However, she was best friends with a girl who was dating a friend of mine, so I saw an ‘in’…
Somehow, my friend’s girlfriend managed to convince Sarah to join the three of us for dinner together to a restaurant (which was a big deal, since we were poor students). After dinner, we all went back to my place (my room, since I was living in a student residence hall) and after a period of talking and drinking, my friend and his girlfriend made their excuses and left, leaving me and Sarah alone.
We sat together and chatted (her on my bed and me on a chair), and at a certain point, I managed to sit next to her on the bed.
And there I sat… and sat… and sat. I was too afraid to make a pass at her (I was thinking “What if I move in for a kiss and she says “Uh, no, I’m not into you” and I’m horribly embarrassed”) and so we chatted, 6 inches from one another for 40 minutes. Eventually she figured out that I wasn’t going to make a move and she left.
The next day, my friend’s girlfriend called me and said that Sarah had actually thought I was cute, but that by not making a move, she’d figured that either I just wasn’t that into her or that I was a sad, sad man with no guts. Either way, I’d blown my chance. I felt like saying the obvious (“Why the fuck didn’t you tell me before we went out that she liked me!”) but I refrained. I did see Sarah again quite a bit, but she never showed any interest, and obviously, I really had blown my chance.
So 20 years on (happily married for 9 of them), I still look back and regret not making that move. Randomly, I recently saw some photos on Facebook form a mutual friend of a group of us (including Sarah) and it all came flooding back…
It’s weird, because this was someone who I knew for a few short years during college, when I was young, and yet it had a profound effect on me ever since. After that, I’d like to say that I was more ‘forward’ than before (not aggressively so, just more along the lines of “It’s better to regret doing something than not doing something”), but this really did change me. But yet I regret it. Ah, Sarah…
So, anyone else want to share, or is it just me? If anyone else throws in their story, I’ll add my second regret story - less teenage sob story, more interesting.