Cast of Caricatures

Story Sent in by Craig:

I live about two towns away from a popular tourist city, so I usually try to avoid it. But Debra said she wanted to go there for our first date, so we went.

Dinner itself and a moonlight stroll by the beach went pretty well, but then we happened upon a caricaturist. Debra was really excited about having our caricatures done. I didn't really want to do it, but she convinced me to sit with her. The artist went to work.

When the caricaturist was done, she took the picture off her easel and showed it to us. I was surprised, as it was actually not a bad likeness of us.

Debra was insulted. She said, "We're not paying for that."

The caricaturist was understandably upset. Debra yelled and said that the picture looked nothing like her at all. I ultimately paid the artist for her work, but Debra insisted on tearing her picture out of it.

I didn't like that idea, as I had paid for the picture and I wasn't about to walk away with only half of it. Debra yelled herself hoarse at me, demanding her picture, threatening to sue me if I kept it. She ultimately lost the fight, as I hung onto the picture (I ultimately ended up cutting her picture out of it on my own) and didn't ask her out again.


  1. Is anyone else reminded of that one episode of Daria where the fashion club has a caricaturist draw them together and hate it? Then try to sue him, undermine him, or find someone to break his kneecaps? It's almost like this is the date version!

  2. I NEVER get caricatures of me done anymore, as I ultimately end up looking like an 8yo girl doing something ridiculous like playing "Hamlet" or randomly skateboarding. I'll save my money for other things, like photo booths where I can wear silly hats and throw up gang signs.

  3. @ Nikki - Yeah, I understand. That last caricature of you murdering the caricature artist was just a little too close to home/police sketch artist territory.

  4. Did Debra know what a "caricature" was? Because if she thought it was supposed to be a legit portrait, that makes this date even more unintentionally hilarious.


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