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People have written infinite pages about the chemistry between movie couples like Stanley and Stella Kowalski (Marlon Brando and Kim Hunter) in A Streetcar Named Desire or Scarlett O’Hara and Rhett Butler (Clark Gable and Vivien Leigh) in Gone with the Wind. While we can’t deny the magic those iconic romances have lent to the silver screen, some of our favorite couples in film are the awkward pairings that don’t quite fit. Many of these twosomes are a complete casting mismatch, but each one has the added burden of overcoming some unfortunate and uncomfortable narrative situations. See what flawed film couples we sent a Valentine to after the break. Feel free to add your own favorites in the comments.

Annie Walker and Ted / Annie Walker and Rhodes

Facing her 40s, recovering from a breakup, and mourning the loss of her business, Kristen Wiig’s Annie Walker in Bridesmaids winds up in a no-strings-attached relationship with Jon Hamm’s awesomely jerky, Ted. The first time we meet him, he can’t wait to kick Annie out of bed. “This is so awkward. I really want you to leave, but I don’t know how to say it without sounding like a dick,” he tells her. He’s a real jerkface — but Annie keeps crawling back to him, hoping the sex will lead to something more. It’s painful to watch, but things aren’t any less awkward with her new potential beau, Officer Rhodes. He does and says all the right things, but Annie isn’t receptive to his kind and loving gestures. The disastrous maid of honor and frustrated traffic cop eventually overcome their messy, uncomfortable interactions and find love, but it wouldn’t be a Judd Apatow-produced film if the matchmaking felt any less like having your teeth pulled.