Pretty Ugly

Story Sent in by Reggie:

There were a couple of red flags in my first messages from Sarah. She was self-deprecating to an extreme. At first I thought she was kidding around until I realized that she had a seriously low opinion of herself. I did my best to bolster her self-esteem, but that didn't work. She was otherwise really nice and I thought that going out on a date with her would be a nice ego boost for both of us. Maybe she wasn't that bad in person.

Nope. She was worse. No later than three minutes after we sat down to coffee she asked, "How ugly do you think I am?"

Sarah was slightly overweight but had a pretty face, gorgeous blonde hair, and a nice smile. "I... I don't think you're ugly at all. You're quite pretty."

She countered with, "What's that supposed to mean?"

"It means I think you're pretty."

She said, "You think? So you don't know? So I am ugly!"

"No! You're not ugly! Can we talk about something else?"

"Because I'm ugly?"

"No! Because I want to talk about something else! Anything!"

"Fine," she said, and she clammed up.

I tried to engage her on different topics but she was clearly miffed at me and barely responded to anything. Since I wasn't about to engage her by telling her how ugly she was I ended the date with a quick, "It was nice meeting you," and I left.

A few minutes after I was on my way home, she texted, "You proved it: you would've stayed if I wasn't ugly."

Okay. Whatever.


  1. A hot chubby girl w/ self-esteem issues? Homeboy hit the jackpot, and let it slip away... SMH...

    1. Throw in some Daddy issues and you got a real sex maniac on your hands.


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