Top 10 Awkward Movie Conversations



Top 10 Awkward Movie Conversations

VOICE OVER: Rebecca Brayton
Script written by Nick Spake.

Awkwaaaaaard! Join as we count down our picks for the top 10 awkward movie conversations. For this list, we're taking a look at exchanges of dialogue that made the characters on the big screen and the people in the audience feel monumentally uncomfortable. From dinner table banter to heated arguments, these conversations come in all shapes and sizes.

Special thanks to our user MikeyP for submitting the idea on our Suggestions Page at WatchMojo.comsuggest
Script written by Nick Spake.

Top 10 Awkward Movie Conversations

Awkwaaaaaard! Welcome to, and today we’re counting down our picks for the top 10 awkward movie conversations.

For this list, we’re taking a look at exchanges of dialogue that made the characters on the big screen and the people in the audience feel monumentally uncomfortable.

#10: I Tried to Kill Myself
“Little Miss Sunshine” (2006)

Failure, suicide, homosexuality; these three concepts are foreign to naive seven-year-old Olive Hoover. She gets a glimpse at how complicated life can be when her melancholy Uncle Frank comes to dinner in this scene from “Little Miss Sunshine.” Although her father wishes to shield Olive from the grim truth behind Frank’s bandages, the rest of the family figures she’ll hear about it eventually. What ensues is a tale that’s as tragic as it is hilarious. Grandpa’s insensitive quips provide the gravy on top of this highly awkward fried chicken meal.

#9: Fancy Sauce
“Step Brothers” (2008)

Will Ferrell and John C. Reilly as two middle-aged men-children still living with their parents? How could that premise not amount to some great awkward humor? At this point in the 2008 comedy, tension is increasing between rival stepbrothers Brennan and Dale. You know somewhere down the line they’re going to clash in a big way. It’s almost more uncomfortable, however, watching their animosity build as Brennan withholds his mother’s fancy sauce one spoonful at a time. Who’d have thought ketchup and mayo could be such a delicate commodity?

#8: Parents Weekend
“22 Jump Street” (2014)

Sometimes the most awkward part of a conversation is letting the obvious go unmentioned. When the undercover Schmidt attends a parents’ weekend, it appears his dorky mom and dad will be the prime source of embarrassment. They’re merely an afterthought, though, when Schmidt finds out his girlfriend Maya is the spawn of his boss. Although their cover isn’t blown, everyone can tell these two have a connection. As Schmidt attempts to make small talk, the Captain restrains himself from jumping across the table and ripping his underling a new one.

#7: Massive Erection
“Anchorman: The Legend of Ron Burgundy” (2004)

The male reproductive organ can be very impulsive, especially when one is in the presence of Christina Applegate, evidently. Professional journalist Veronica Corningstone is the one woman who isn’t immediately won over by womanizing Anchorman Rob Burgundy’s classy hair and pickup lines. When Ron at last convinces Veronica to go out with him, he holds himself back from cheering and jumping for joy. However, the area below his waistline encompasses all the bliss Ron is experiencing in this moment. Ron might not notice his massive erection, but Veronica certainly does.

#6: Peter Asks Gwen Out
“The Amazing Spider-Man” (2012)

Already suffering from poor social skills, the last thing Peter Parker needs is his Uncle Ben humiliating him in front of Gwen Stacy. Once he’s alone with his crush, Peter tries to ask Gwen out on a date without actually saying the words, “Do you want to go out on a date?” The stars have such amazing chemistry, though, they overcome this awkward hurdle. Now that Spidey has caught the girl in his web, it should be nothing but clear sailing for the couple…or not…

#5: Pass the Asparagus
“American Beauty” (1999)

The Burnham family of “American Beauty” is a shaken up bottle that’s about ready to explode. After Lester quits his job, his wife Carolyn tells him off all while maintaining her perfect phony smile. Lester couldn’t care less what she or anybody else thinks, concerned more about getting his asparagus. Caught in the middle of the feud is their daughter Jane, who is forced to stay in her seat and watch her parents’ marriage crumble. It all works up to a climatic moment in which Lester finally shuts Carolyn up.

#4: I’ll Have What She’s Having
“When Harry Met Sally…” (1989)

Having a friendly meal at a restaurant, Harry and Sally start talking about women faking orgasms. When Harry claims he can tell when a woman is putting on a show, Sally goes all out in proving him wrong as a series of sex noises emanate from her mouth. After Sally finishes her passionate performance, Harry and the rest of the restaurant are at a loss for words. The only one with a witty retort is director Rob Reiner’s mother, who scores the most iconic line from “When Harry Met Sally.”

#3: Are You a Virgin?
“The 40-Year-Old Virgin” (2005)

It’s common for a 14-year-old virgin to act like they know all about sex when really they understand nothing about the subject. When a 40-year-old virgin tries to spice up his nonexistent sex life, though, it’s just awkward. At a poker game with his friends, Andy is pressured to share his hottest sexual experience. Drawing a blank, he fabricates a horny ex and describes her sand-filled tits. Of course, his pals can see right through Andy’s charade. With this new information, it’s like they’re seeing Andy for the first time.

#2: Masturbation Talk
“American Pie” (1999)

There’s never been a more awkward father-son duo than Jim and Mr. Levenstein. When Jim’s dad starts to notice that his boy is becoming more conscious of the female body as well as his own, the two have a talk about stroking the salami. That’s just one of several phrases Jim’s dad uses as a substitute for “masturbating,” encouraging his son to find a partner rather than relying on pies. This isn’t the firstawkward conversation the two share and it’s far from the last, but it perfectly sums up their relationship.

Before we have a little chat with our top pick, here are a few honorable mentions:
- Duane Hall
“Annie Hall” (1977)
- Mike Yanagita
“Fargo” (1996)
- Going Down Payment
“Mrs. Doubtfire” (1993)
- Buying Booze
“Superbad” (2007)
- Breakfast
“Knocked Up” (2007)

#1: Funny How?
“GoodFellas” (1990)

Tommy DeVito is a completely unpredictable character, making jokes one minute and making threats the next. And the audience comes to see just how hotheaded Tommy is in this improvised scene from “GoodFellas.” When Henry casually tells his friend that he’s funny, Tommy takes the compliment the wrong way. Making everyone’s skin crawl, the gangster hounds the stuttering Henry for an explanation. Tommy was fortunately just joking around this time, but it’s easy to imagine something so minor setting this volatile funnyman off on a rampage.

Do you agree with our list? What film conversations put you in an awkward position? For more entertaining Top 10s published every day, be sure to subscribe to
Christopher Walken in Gigli!