1. Boogie Nights
The lesson in Boogie Nights is that if you marry a porn star, you’ll probably see them boning someone else on the regular. Even at pool parties. Where other people are watching. And it will be insanely awkward for you.
2. Knocked Up
Sex while you’re pregnant is apparently a tricky endeavor. Mainly when your baby kicks, and reminds you that they’re along for the ride too. Sorry, sorry, that was gross… But Seth Rogen said it first. Sorry.
3. American Pie
We all know what happens to that poor pie…
RIP pie. :(
Nomi and Zack having sex next to neon dolphins is so deliciously bad that it’s good. Good in a “you’ll laugh until you cry” kind of way.
Bennifer is at their pinnacle of awkward when they have sex in Gigli. Not only because the words “gobble gobble” are meant to be seductive, but because J.Lo is a lesbian who inexplicably turns for Ben.
Perhaps “inexplicably” is too harsh a word. I mean, after all, who could resist those tatted up arms?
6. Forgetting Sarah Marshall
It’s weird when you break up and go on an exotic vacation with your new rockstar boyfriend only to discover that your ex is in the next room. Know what’s weirder? When you fake an orgasm to make your ex jealous. (Russell Brand feels me.)
And this other scene where newlyweds Darald and Wyoma have sex for the first time.
7. The 40-Year-Old Virgin
Of all the awkward moments that happen to poor Steve Carell in The 40-Year-Old Virgin, his foot fetish fail ranks pretty high. Not that I can blame him — who isn’t ticklish?!
Remember the senso-rings? Remember how Chris Farley tosses one on Connie’s head, and they get all sweaty and are about to, ya know…? Yeah, that was weird.
Even a man as hot as Jon Hamm can have awkward sex. (That’s comforting, isn’t it?!)
10. Ace Ventura
Sure, it’s funny that an entire animal kingdom is watching Ace get it on… I just feel sorry for them, is all.
11. Devil’s Advocate
This is the scene where Al Pacino (aka THE DEVIL) tells Keanu Reeves that he and his half sister should fornicate so that they can produce the Antichrist. If incest isn’t awkward enough for you, the fact that Pacino watches right behind them will be.
12. Shoot ‘Em Up
It’s true that Shoot ‘Em Up is a dark comedy, but nonetheless this scene is just too crazy to leave out. If only because Clive Owen manages to expertly kill his would-be assassins, all while managing to stay inside “D.Q.” Just saying.
13. Howard the Duck
It’s one thing to see Roger and Jessica Rabbit together, but it’s quite another to see Howard the Duck make sexual innuendos with a live-action person. This is bestiality at its utmost grossest.
To be fair, the sex scene in Greenberg is intentionally awkward. With Florence saying things like, “I’m wearing kind of an ugly bra,” and “Do you hear a train? Is that a train? I get kind of nerdy,” mid-coitus. Nonetheless, this is awkward times a zillion.
15. The Room
Lisa, you are tearing me apart! Mostly because the sex scenes between you and Johnny last for painfully long amounts of time, and involve a bit too much simulated thrusting. Not to mention the total creeper who won’t seem to leave you two alone…
16. My Super Ex-Girlfriend
Did you know that you can have sex while flying with your superhero ex? It happened to Luke Wilson, and it was the least sexy mile high club ever.
17. Bride of Chucky
Ugh. Doll sex. It’s just the absolutely worst.
The problem here is less the vigorous sex and rubber suits, and more the choice of Leonard Cohen’s original version of “Hallelujah” playing in the background. It’s just weird.
19. The Matrix Reloaded
It’s not so much that the idea of Keanu Reeves having sex is awkward. (Though, admittedly, it is. This is his second mention on the awkward list.) It’s more that he has sex in some cave underneath a nightclub, while everyone else is upstairs dancing.
“Oh, hey, we’re interviewing you for this job, but we’re also going to have this woman give you a blowski while you work. Cool? Great.” Except it’s weird to see John Travolta watching Hugh Jackman’s O-face… right?