1. Boogie Nights Via youtube.com 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 Tap to play or pause GIF Tap to play or pause GIF Via hulu.com 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 Tap to play or pause GIF Tap to play or pause GIF Via youtube.com We all know what happens to that poor pie... RIP pie. :( 4. Showgirls Tap to play or pause GIF Tap to play or pause GIF Via youtube.com 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. 5. Gigli Via makeanddeux.com 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 Tap to play or pause GIF Tap to play or pause GIF Via youtube.com 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. Tap to play or pause GIF Tap to play or pause GIF Via youtube.com 7. The 40-Year-Old Virgin Via adventurepaul.com 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?! 8. Coneheads Via youtube.com 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. 9. Bridesmaids Tap to play or pause GIF Tap to play or pause GIF Via youtube.com Even a man as hot as Jon Hamm can have awkward sex. (That's comforting, isn't it?!) 10. Ace Ventura Tap to play or pause GIF Tap to play or pause GIF Via youtube.com 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 Via youtube.com 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 Tap to play or pause GIF Tap to play or pause GIF Via youtube.com 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 Via youtube.com 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. 14. Greenberg Via okinawaassault.wordpress.com 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 Tap to play or pause GIF Tap to play or pause GIF Via gifmovie.tumblr.com 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 Tap to play or pause GIF Tap to play or pause GIF Via youtube.com 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 Via pete975.wordpress.com Ugh. Doll sex. It's just the absolutely worst. 18. Watchmen Via 1heckofaguy.com 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 Via youtube.com 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. 20. Swordfish Via realboysdontblog.wordpress.com "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? 21. Breaking Dawn Tap to play or pause GIF Tap to play or pause GIF Via fanpop.com Oh, vampire virginity — how uncomfortable it is! We don't see much in this sex scene; a few flashes of thigh here, a broken bed frame there. But it's all enough to feel intensely awkward.