Although pick up lines rarely work in the real world because they are often too cheesy and contrived to be endearing, they make for excellently awkward moments in film. Most of the time, if not always, these pick up lines lead to rather unfortunate scenarios for everyone involved. When saying these lines, instead of appearing suave and charming as planned, they often come across instead as foolish and socially inept. What are some of the most cringy pick up lines in film history that make us crack up with laughter? Read on to find out!
“So, do you like cheese?” - She’s The Man
“My favorite’s Gouda!”
This is pretty much the line that made She’s The Man such an iconic film that we still praise to this day. Amanda Bynes kills it in this movie by disguising herself as her brother Sebastion, in order to play soccer at his boarding school.
She teaches her roommate a.k.a. Channing Tatum how to talk to girls, and Bynes’ character suggests that he start off by strike up a conversation about cheese. It’s definitely an unusual conversation starter, but, hey, who wouldn’t want to talk about cheese with Channing Tatum? Sound like an awesome time to us.
“Hey not Air Marshall John, wanna get back in that room and not rest?” - Bridesmaids
This hilariously cringy pickup line comes from the one and only Melissa Mccarthy in Bridesmaids. In the 2011 comedy, she plays Megan, a character who is absolutely shameless when it comes to what she wants.
This is made very clear in the scene when she tries to seduce an air marshall on an airplane, who claims not to be one. Megan is brilliant, so she is able to see right through his lie. Funnily enough, air marshall John is Mccarthy’s husband in real life so it makes their flirtatious interactions all the more hilarious.
“I would like to extend to you an invitation to the pants party.” - Anchorman
Oh, Steve Carell. How is he so good at playing awkward characters with little to no social skills? In Anchorman, he plays the hilariously clueless character named Brick Tamland who doesn’t know what’s going on 100% of the time.
This is honestly what makes him the most lovable character in the whole movie. He ends up asking Veronica (played brilliantly by Christina Applegate) if she would like to go to the pants party. Of course, he was set up to ask this. As expected, Veronica declines the invitation.
“Is your muffin buttered?” - Mean Girls
This is one of the most cringe-worthy lines in all of Mean Girls, and that’s saying something considering the whole “Grool” incident. Cady gets asked this in the cafeteria by a total stranger, and, as sad as it is, this is not uncommon behavior amongst high schoolers who don’t know any better.
Cady has no idea what he’s talking about, and luckily Regina and the rest of The Plastics shoo him away before he can get more graphic with his awful food puns. Thank god for small favors!
“Oh God, you taste like my vitamins! I think I’m in love with you!” - Booksmart
This line is said by Billie Lourd’s hilariously eccentric character in Booksmart. In Olivia Wilde’s directorial debut, the film centers around soon-to-be high school graduates, Molly and Amy. These characters discover how much they have missed out on in high school, and they try to live it up as much as they possibly can before graduation.
One of their wild encounters includes the girls attending a party with Lourd’s character, Gigi, who delivers this cringe-tastic pickup line to Amy. As if the situation couldn’t possibly get any more awkward than it already was!
“Allow myself to introduce… myself.” - Austin Powers
Austin Powers is a hilarious movie trilogy designed to satirize the spy film genre of the 1960s. In contrast to the suave charm of James Bond, Austin Powers pretty much represents the exact opposite of this archetype, yet we are somehow still drawn to him to this day. He is filled with hilarious (and cringy) pickup lines, including “shall we shag now, or shall we shag later?” and “allow myself to introduce… myself.” Gotta love Mike Myers!
“I like the parts of your face that are covered with skin.” - Anchorman 2
When you pair up Steve Carell and Kristen Wiig, you know you’re in for the big laughs. This is most certainly the case in Anchorman 2 when these bizarre characters meet and instantly fall in love. It is easily one of the funniest scenes in the entire movie, and who better than these two comedy legends to play awkward individuals falling in love? To us, this line is incredibly cringy, but to them, it is pure poetry.
“I see you’re drinking 1%, is that ‘cuz you think you’re fat? - Napoleon Dynamite
“I see you’re drinking 1%. Is that ‘cause you think you’re fat? Cause you’re not. You could be drinking whole if you wanted to.”
If we were to rank movies for the title of “most awkward,” Napoleon Dynamite would undoubtedly be crowned first place. This film is designed to be a total cringe-fest and it definitely succeeds in what it seeks out to do. Napoleon says this line to his crush in an effort to flatter her, and it isn’t exactly what most of us would consider a “suave” pick up line. Luckily enough for Napoleon, his crush is just as strange and awkward as he is.
“I know not who you are, nor how I came to find you, but, can I just say… hi, how ya doin’?” - Tangled
This line comes from the beloved Flynn Rider in the Disney film Tangled. Flynn believes he is a serious charmer, and he lives to make the ladies swoon with his “smolder,” but Rapunzel doesn’t buy into his act. She ends up falling for Flynn once she gets to know him and he lets go of his whole self centered act that we are met with at the beginning of the film. Yet, despite his growth, this pickup line perfectly describes Flynn’s persona in the first few acts of Tangled.
“This is awkward. Not you’re awkward, I’m awkward. You’re gorgeous. Wait, what?” - Frozen
This line is said by Anna in Frozen, and one of the reasons this Disney film became such a smash success was due to how realistic these characters were compared to other Disney Princesses we are used to seeing in these films. We are so used to seeing princesses in Disney movies who haven’t a single flaw and are constantly elegant, yet Anna’s cringy introduction to Hans in this scene is so refreshing because it’s human.
