I asked a woman out at work. Even as I walked toward her I was thinking “this is stupid, I’m going to ruin it”.

Then I asked if she’d ever like to catch a comedy show with me. She asked why I asked her. I said I thought she was funny. She said she’d think about it. I walked away for a few seconds, came back saying “this is stupid. This is where we work” and she agreed, saying it would go against her rules. I said “pretend I never asked”, knowing it was impossible.

Later on we texted, and she said something like “I’m too busy for a social life (what a gentle let-down), but we can be work friends”.

And get this … she’s actually a work friend now. We work in a big complex and cross paths sometimes, and it’s fun when we see each other. She’s funny and sweet and somehow supportive just with her presence. Like I’ll be having a rough time with a client or whatever and she’ll come by and just make eye contact and it feels like an old friend just walked in. Despite me having known her for just a couple months, she feels like an old friend.

I dunno. I totally fucked up, broke my own rule and hers, and it still produced something valuable.