IT’S UNCOMFORTABLE: 10 Awkward Movie Scenes You Can’t Stop Watching

Awkward moments. They happen.

Waving back to a person who’s waving at someone else. Congratulating a not-pregnant woman. First dates. Anything involving holidays and in-laws.

But we’re not here to talk about those moments.

No, we’re here to talk about the 10 most awkward scenes from movies of yore. And if you pay close enough attention, you may just learn a thing or two.

Or at the very least, figure out that there’s no right way to punch a girl in the boob…


The Awkwardness: Within the context of the movie, it’s kind of a beautiful scene. But unfortunately, that’s not enough to keep it out of awkward’s reach. We’re talking, of course, about when Bill Murray, God bless him, performs a less-than-riveting rendition of Roxy Music’s “More Than This” in a Tokyo karaoke bar.
The Takeaway: If you’re Bill Murray: keep being you. If you’re you: keep not singing karaoke unless you can sing karaoke.

The Awkwardness: When Evan calls Becca “Miss” and then “Sister” and then accidentally punches her in the right boob.
The Takeaway: Hey, listen. We get it. It’s fine if you don’t know what to do with your hands while asking a girl out. Especially if you’re a high school student in a 2007 coming of age comedy produced by Judd Apatow. So maybe just keep them in your pockets.

The Awkwardness: Vince Vaughn’s character, Ricky, finds himself on a plane to JFK in first class. And then he finds himself unable to not repeatedly hit the flight attendant call button just to make sure everything’s actually free up there. What follows is nothing short of pure awkward delight.
The Takeaway: Yes, everything’s free up there.

The Awkwardness: You know the one. The dinner table scene with the teets and the prayer and the mother’s ashes. It’s horrifying. And by horrifying we mean… well, horrifying.
The Takeaway: While attempting to make a good first impression with the soon-to-be-in-laws, be humble. Keep it short. Don’t showboat. Don’t use hand gestures. Don’t desecrate anyone’s remains.

The Awkwardness: Philip Seymour Hoffman was a man who owned his craft. So when the Boogie Nights script called upon him to act out what was arguably the most uncomfortable scene in recorded history… just watch it and hope that one day you can move on.
The Takeaway: Whatever it is you’re into, don’t half step it. Just own it. We like your car, too, Scotty.

The Awkwardness: Favreau puts on an awkward clinic in the scene where he leaves 5,782 voicemails (give or take a voicemail) for a girl he just met that same night.
The Takeaway: Slowly. Calmly. Step away from the phone.

The Awkwardness: It’s all pretty low-hanging fruit when the discussion turns to Napoleon Dynamite. And surprisingly enough, the scene in question doesn’t even star the boy wonder himself. It’s when Kip gets gently yet awkwardly smacked around at Rex Kwon Do in front of his peers. It’s delightful.
The Takeaway: Private lessons.

The Awkwardness: “Funny how? How am I funny? Funny like I’m a clown?” Yeah, that one. The tension between Ray Liotta and Joe Pesci is palpable.
The Takeaway: Don’t go out to dinner with mobsters. And if you must, keep your mouth shut.

The Awkwardness: The part when Paul Rudd comes home and overhears his wife and her friends talking about how he has no friends. The obvious solution to this conundrum: waltz in the room with a tray of root beer floats.
The Takeaway: It’s always best to begin the hanging-out-with-Jason-Segal-and-going-to-Rush-concerts process early in life.

The Awkwardness: Stiller again. This time with a zipper malfunction that ended with his prom date’s mom, his prom date’s dad, a cop, a police officer and, well, every single neighbor seeing his “Frank and Beans.” We’ll make it through this together. Just remember, it’s all make believe.
The Takeaway: This is why they invented the button fly, we assume.


For more great movie moments. check out (arguably) the best Alec Baldwin movie scene ever.