What's your worst story of blowing it with someone that you felt you had romantic potential with?

The Failed Courtship Attempt by a Socially Awkward Frat Boy

  • Joined fraternity

  • Met sorority girl. Girl asked me to be her date for a formal Greek event. I politely declined, assuming it was a joke

  • Girl attempted to talk to me every now and then, but no meaningful conversation achieved because she is super popular and we always get interrupted. After a full year of failed/interrupted small talk conversations, I finally asked for her number while she was playing with my phone. Got them digits, and the girl told me I play hard to get. wat

  • Cue srs legal troubles o shit (I was framed!)

  • Sister joined girl's sorority. Asked girl to look after my sister if I go to jail. She promised she will. <3 Justice prevailed, so no jail time phew

  • Girl suggests dinner together a few months later. Dinner was great!

  • Proceed to ask girl if she is free on 3 separate occasions - she is too busy all three times. Hint taken. I graduated and gtfo of college, whatevs yo pce

  • Dad died a year later

  • Girl shows up at my dad's memorial service. Even though I already kind of got turned down by her, I figure there'd be nothing to lose by asking her out for a coffee. Most likely taking pity on my situation, she agrees. I foolishly think of it as a date...

  • She mentions over coffee she is looking for a boo who can fluently speak a certain dialect. I know she knows that I speak it :O

  • Asked her to get dinner. She said yes! However, started to get vibes that she wasn't nearly as into this as I was. Vibes confirmed that night at the bar when she ignored me to talk to another guy

  • Recognized that I was played, but decided to go for broke, anyway. Called her up, told her I was aiming for something more than platonic, and asked her out on a "date". She gives me a well-rehearsed "you're such a nice guy, but I'm not looking" speech, complete with sniffling to indicate emotional distress

  • So impressed by that acting that I cannot even be mad

In retrospect, maybe she was just really nice and I was reading way too much into things. This is unfortunately the closest I ever got to dating someone.

gaiz i need halp pls

/r/AskMen Thread