This looks troubling. It's a scene from The Simpsons episode "Married to the Blob."
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Homer offers Comic Book Guy dating advice on The Simpsons. "Married to the Blob" is the tenth episode of the show's 25th season.
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The Simpsons Season 25 Episode 10 Quotes

Nerds don't get girls!

Comic Book Guy

The closest thing I have to a father is the Obi-Wan doll in my store, and he comes from a race of celibate knights so...

Comic Book Guy