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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.
Christian & Gina, Nip/Tuck (2008)
These two carry on a love-hate sexual relationship for five seasons of Ryan Murphy's twisted series, with most of the hate falling on Christian's side. Gina, a sex addict with borderline personality disorder, usually has a bomb to drop — like claiming to be pregnant with his child (when he's not the father) and revealing that she has HIV and he (and all his previous partners) should get tested. When she devises to win him back and he's finally had enough, Christian fucks her right off the edge of a building.
Lesson: Check those railings — and your lover's mood — before dropping trou on a rooftop.
Jess & Paul, New Girl (2011)
Burned by a cheating ex (the only guy she's slept with since before Obama was in office), Jess is all nerves climbing into bed with Justin Long's Paul. After she consults the gang, picks up some soft-core fetish gear with Cece, and studies Schmidt's porn for pointers, it's Winston who doles out the best advice: Just be yourself. (This being Jess, awkwardness ensues, regardless.)