9. Two and a Half Men: Lyndsey, Alan and Walden
This threesome isn't exactly a sexy one but it sure is hysterical to watch unfold. In episode 3 of season 10, Alan (John Cryer) and his girlfriend Lyndsey (Courtney Thorne-Smith) agree to a deal: he gets a threesome with another woman and she gets a threesome with Walden (Ashton Kutcher). Walden and Alan hesitate but eventually agree to it and comedy ensues. The two men are in their underwear on the bed waiting for her to freshen up. The contrast between Walden's tanned, toned physique and Alan's pale and flabby body is brutally funny on its own and then gets highlighted when Alan tries to sit like Walden to look better. While they are waiting, the men reconsider and awkwardly convince themselves that what they're doing is not weird. Lyndsey comes out of the bathroom, but immediately goes for Walden. As the two are kissing, Alan struggles to figure out what he's supposed to do. He ends up awkwardly petting and licking her. The action is short-lived however, as Walden breaks down about his ex-girlfriend. The threesome is painful to watch but it's also incredibly amusing and in a way, realistic. It points out the very real danger of what could happen if one partner grants the other a threesome, especially when the outside person is much better looking than them.
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