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Bridget Jones's Diary (2001) This adaptation of the best-selling 1996 book of the same name features Renee Zellweger as Bridget Jones, a charmingly klutzy thirtysomething whose search for Mr.
Right comes down to her suave boss Daniel (Hugh Grant) and her childhood friend Mark (Colin Firth).
He's Just Not That Into You (2009) This adaptation of the 2004 best-selling book He's Just Not That Into You is packed with cringe-worthy dating moments, but the worst comes when hyper-clingy Gigi (Ginnifer Goodwin) attends a speed-dating event.
As one potential suitor walks away with a vague promise to get in touch, Gigi desperately hounds him for specifics until he abruptly shuts down the conversation.
50 First Dates (2004) Imagine meeting someone at breakfast, spending the entire day together without a care in the world, and waking up the next morning in their bed to them screaming because they don't know who you are.
Things predictably take a turn for the worse then the LAPD shows up and Dylan can't jump down to safety, leading to an awkward evacuation via helicopter broadcast on national TV.
Fatal Attraction (1987) Nearly every moment in the psychological thriller Fatal Attraction, about a deranged woman (Glenn Close) who stalks a married man (Michael Douglas) after a weekend fling, is awkward, cringe-inducing or downright disturbing.
In one of the film's most awkward scenes, Lucy arranges a string of dates at a local bar that devolve into gross-out displays of how awkward internet dating can be.
But just as Bridget gets her chance with Mark, he notices her diary and storms out after reading the insulting things she's written about him.
How To be Single (2016) Dakota Johnson is the star of How To Be Single, a romantic comedy about the ups and downs of dating in New York City, but Alison Brie steals the show as Lucy, who is on a data-driven quest to find The One.