Your biggest sexual or relationship blunder?

Being a total jag to my first real girlfriend. Still haunts me to this day. I'd like to punch my younger self in the face for this one, repeatedly.

 

Oh man, I TOTALLY BLEW IT once. It still makes me smh after all these years.

Girlfriend #1 asked me to invite girlfriend #2 over to watch a movie. Just the three of us in our apartment with drinks, watching the movie. Nothing happened. Didn't make a move. Why? Because I didn't pick up the hints until AFTER girlfriend #2 left later on. The next day, girlfriend #1 says "So, I was waiting on you to make a move for a threesome but you never did so....that's that."
I was shocked. So I asked girlfriend #2, she says "yeah, you didn't make a move. So I said screw it.".
Yep....I'm an idiot.
I did, however, marry one of them.

 

So the glass is half full. Cool.

 

Yeah, despite all my depression and darkness, I still see things on the bright side from time to time.

 

19. A girl I talked to plenty, who I thought was out of my league, suddenly expressed interest and totally caught me off guard. Had I got that one right I might have made it with a red head girl in a Chevrolet (like in the Billy Joel song Keeping the Faith). I don't know if I'd have been better off with or without her.

 

Blunder.
Spending 20 years with a girlfriend who I didn't love and didn't force the issue of breakup because it wasn't totally horrible until the last couple years.
What a fucking waste of time.