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It doesn't. It's a fat guy who's laid 3 women's idea of a rom-com. Ben Affleck Turns A Lesbian could've been a funny and edgy movie and, to be fair, it was when I watched it in my teens. Older and (a bit) wiser, it doesn't work.Chasing Amy was surprisingly good. Not sure how well it holds up.
The scene where Affleck is whining to win her over in the rain is embarrassing. Again, when you're 14 (or a fat dude with no game) you think "Hey, that long speech would definitely work!" When you're a bit older and have actually fucked, you realise a wordy, beta speech like that would dry up any pussy faster than a pants-shitting incident. And Jason Lee's character is gay suddenly because he's an asshole? And don't get me started on the militant gay black dude. It's the kind of movie Fat would think is a realistic representation of sexual politics.