The other answer to the rape question.
This is deeper than a simple "did he rape her" question.
Spoilers, of course:
Shawn raped Sara, not Michael. My theory rests on five important clues:
1. Shawn, the "nice guy" who didn't drink DID do drugs. When he came out of the bathroom bar and started clearing his nose, it's a tip off that he was snorting some sort of drug. Even more telling was this was said right after someone said he didn't drink... never said anything about drugs.
2. At the club, a drunk Shawn gave Sara a drink that would make her "feel better" when it looked like Michael left. Michael comes back and whisks her off to his misfortune.
3. When Shawn is having intercourse with Emma later outside the bar someone says that there are some men who don't make it look like they have orgasms when they do. Throughout the movie there is talk of men "needing" to get off, even to the point of penises falling off if they don't. This seems like a way to trick the viewer into thinking that Shawn did have an orgasm when he actually did not.
4. Shawn takes of his condom! Mr. Nice guy who doesn't even kiss on the first date brought at least one condom. This guy was expecting to get lucky, else his penis would fall off.
5. At Sara's house, both Sara and Michael blacked out at the SAME TIME. Neither could remember the story to defend themselves.
Here's what I believe happened: Shawn hasn't "gotten off" in a long time and starts falling for Sara. Sara wants to get laid and attaches to Michael. Shawn gets jelous and decides to drug her. Outside of the club and still needing to get off, Shawn has unsatisfying sex with Emma and he doesn't climax but fakes it because she already did long ago. Shawn discards his empty condom and drives to Sara's house where he witnesses both Sara and Michael about to pass out on the beach. Sara leaves her door open and Shawn pounces when they're both knocked out from drinking from the same bottle Shawn gave her. He does a little rape, dumps Michael on the street, then goes home thinking they would both assume they had sex.
I'd always thought about writing a short story where the REAL antagonist isn't spoon fed at the end of a twist, but instead you'd have to figure it out yourself AFTER reading. Perhaps I was beaten to the punch.
PS. Don't get sidetracked by any holes in my theory, such as the question of where Michaels semen went they both claimed he wore no condom, because that would just tear this whole thread into shreads. I'm sure we can figure that one out.
"A closet intellectual, he acts dumb to impress women."