Back in 2004 or so a friend from work and I decided to go to Detroit to see a football game.

The Lions sucked but it was exciting to go. To top it off we managed to score tickets to see The Beastie Boys the same weekend.

The concert was awesome and the game was a good time. After the game we headed to The Hard Rock for a few drinks.

My buddy considered himself a ladies man and started giving our waitress the once over. A few beers in he was in full on pick up mode. Every time she left the table he told me I’d need to find somewhere else to sleep. She started slipping us free drinks and suggested we tag along when the staff went out after her shift. My buddy’s radar was going off like crazy and he started making elaborate plans.

So we headed off with the crowd. When we arrived the waitress and my friend disappeared while I sucked on a beer. After about half an hour he was back again giving me the low down on his plan to take this girl back to the room. As he was filling me in the waitress returned with a couple of girlfriends and asked what we were up to. This was when buddy went in for the big question…”What if you and I go back to my room?”

“Oh…didn’t you know? I thought I told you. I’m a lesbian. I like girls and this is my girlfriend.”

Well the look on his face was memorable to say the least. I on the other had was secretly grinning my face off.

After the shock wore off he started to talk with her. I’m not sure what they said because by this time her girlfriend had asked me to dance. Suspect she didn’t want to be in the middle of a confusing conversation with a confused hetro man.

Out on the dance floor I played back the whole story to her girlfriend. She was talking to me about how it sucked being a wingman and how she understood why I had a shit eating grin back there.

“Yeah” I said. “Considering he spent the whole night saying he was ‘gonna get some for sure’”.

“Oh?..like this?” at which point she grabbed both my hands and parked them straight on her chest. Complete with a great squeeze.

A split second later I turned to see my buddy staring back at us, with his jaw on the ground. I don’t think I’ve ever seen an ego deflate so fast in my life.

All he kept saying for the next week…”I knew she was a lesbian all the time.” That or “Shut up!”

I love winning sometimes.

#confessional