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Felicity & Noel, Felicity (1999)
Getting it on in a dorm is always tricky. But even Team Noel diehards questioned their allegiance after the pair's awkwardly drawn-out plan to finally do the deed goes awry. Results: the death of an iMac, a Christmas-tree fire, and no actual sex. Score one for Team Ben.
Lesson: There's something to be said for spontaneity.
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.