Member-only story
Owning Up to it
That Time I was the Worst Wingman Ever
If you’re going to fail, fail epically
I’ve had a lot moments I’m really proud of.
This is not one of them.
Back in my late 20s, my buddy D and I took a snowboarding trip to Colorado. We spent the night in Boulder so he could relive his college days he still longed for.
At the time, D was a lot better at meeting girls than I was. I was shy and awkward and inexperienced. I’d have some pretty good nights here and there, but more often than not I’d get stuck inside my head and crash and burn.
It was frustrating and depressing.
But I was determined to get better. For the previous six months I had embarked on a steep climb, and the only way to get better was to get out there and keep working at it, no matter what.
We started off in a margarita bar called The Rio. Great vibe in this place. We were pounding margaritas and feeling just perfect. For some reason, I decided that D should be called “Rudy” for the rest of the night, and whenever he drank, we’d chant “Rudy… Rudy… Rudy..”
At the table next to us were a bunch of girls. They were cheering us on, and I was feeling into it, so I turned around to talk to them.
