This happened on Tuesday night

Because I’m always willing to approach and talk to women, sometimes one of my friends will jokingly egg me on to approach attractive women around us.

We were at a small hangout spot and it was pretty dead. There was my small group (my aforementioned friend, his girlfriend, a mutual friend & myself) and two women hanging out together across the room.

My buddy said, “I bet you won’t go talk to those women.”

I said, “Say less.”

I walked over and struck up a convo. One of the women didn’t seem very interested in chatting, but the other one was responsive, so I primarily talked to her.

Basically, where the conversation went sideways was when I had them guess my age (they thought I was in my 20’s, but I’m 31). They said they’re older than me (both in their 40’s, but they looked like they were in their 30’s still) and I replied, “You both look good for your age!”

I think that’s where I lost them. They didn’t speak much after that and one of them announced shortly after “Well, it was nice meeting you. We’ve gotta go.”

I wanted to apologize, but I just walked back to my group and sat there thinking about what I said wrong.

I believe it had to be the “look good for your age” part.

I think they got annoyed that I implied they were only attractive for being 40+ yrs old. I accepted the L that night, but every time I think about how awkward it got after I made that comment, I literally cringe.

Every approach is a learning lesson, though, right? 😅 ... Right...? 😭