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Jerry & Elaine, Seinfeld (1993)
After Elaine confesses that she never had an orgasm when she and Jerry dated, he begs for 30 minutes to prove his skills between the sheets and save their friendship. Elaine thinks it's a bad idea — and she's right. Jerry's too psyched out to perform and Elaine gets some quality time with a magazine.
Lesson: If your best friend is also your ex, maybe think twice about revisiting that honey pot.