Pretty Ugly

Story Sent in by John:

Kelly brought her high school yearbook to our first date. Over dinner she flipped through it, opened it to the page with her senior photo, and asked me, "Was I prettier then or am I prettier now?"

I told her, "You're prettier now."

She liked that answer. She closed the yearbook, said, "Good," and put it away.

About five minutes later she asked me, "Am I prettier now or was I prettier five minutes ago?"

I said, "You're even prettier now."

She gave me a nice smile and I hoped she'd thenceforth shut up with the prettiness questions.

A little bit after that, she asked, "Am I prettier now or was I prettier the last time I asked you how pretty I was?"

I replied, "Honestly, I think you're pretty now, five minutes ago, and even back in high school." I thought that was a pretty good answer.

Apparently, it wasn't. She gave me a horrified look and opened up her yearbook and said, "I was an ugly, pock-marked mess in high school! You mean to tell me that you think this is pretty?" She pointed to her high school photo, which wasn't really at all ugly or pock-marked.

I said, "I think you're pretty. Can we end the discussion?"

She slammed the yearbook closed and said, "Never mind. You think I'm ugly. All there is to it."

I said, "I don't," but I must not have been convincing, or else I was tired of the conversation. But she didn't take that well, either.

She said, "No, I'm the ugliest girl you've ever seen. You might as well just come out and say it. You've said everything but."

I said, "Okay. How's your soup?"

She replied, "Perfect for an ugly girl."

After dinner we took a brief walk and she asked, "Are you sure you're okay being seen with someone so ugly? I don't want to embarrass you or anything."

I said, "I think you look fine. If anything about you will embarrass me, it'll be your personality."

She totally flipped out at that. She said that she had a loving, good-natured, wonderful personality and that I'd do well to grow up. Yes, I'll be noting that. And that was our only date.


  1. Kelly seems pretty.....dumb. By the way, does this font make me look fat? Sometimes I use comic sans bold and it goes straight to my hips.

  2. I hope this story is true.

  3. OP missed out. Women with self esteem issues are a GOLD MINE.

  4. Kudos to OP. Acted gallantly at first, but when she kept on going about with that nonsense, he had a great brutally honest riposte which, even if hurtful, was not overly nasty.

    This kind of people are usually manipulative and all their efforts are spent either finding faults in others to belittle them, or creating situations to play the victim. These people are toxic.

    She probably really deeply hates OP because he did not fall in the trap...


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