15 Romcoms Where We Aren’t Exactly Comfortable With the Relationship

Romantic comedies have convinced us to root for some pretty questionable couples. A little dishonesty, a ruined wedding, or an elaborate plan to manipulate someone apparently becomes acceptable when the soundtrack is good enough. And somehow, we’re still cheering when the characters finally kiss. Some of these movies are genuine favorites, which makes revisiting their relationships even stranger. The chemistry is there, the jokes still work, and then you remember how the couple actually got together. A few romances involve people who probably shouldn’t be dating at all. Others simply have enough red flags to make their happy endings a little difficult to celebrate. Here are 15 romcom relationships that deserve a second look. 13 Going on 30 (2004) Jenna has the mind of a 13-year-old inside a 30-year-old woman’s body, yet she’s falling for an adult Matt who’s already engaged. That’s a lot to overlook. The Proposal (2009) Margaret threatens Andrew’s career unless he agrees to a fake marriage to prevent her deportation. Somehow, a boss blackmailing her assistant becomes the beginning of a love story. Never Been Kissed (1999) Josie returns to high school undercover as a student and develops feelings for a teacher who believes she’s a teenager. The eventual reveal doesn’t make the setup any less uncomfortable. Love Actually (2003) Mark confesses his feelings to Juliet using handwritten cue cards, despite the small detail that she’s married to his best friend. Christmas apparently makes boundaries optional. How to Lose a Guy in 10 Days (2003) Andie deliberately tries to make Ben dump her for a magazine article, while Ben secretly bets he can make her fall in love. Neither knows they’re dating a walking assignment. The Wedding Planner (2001) Mary falls for a charming doctor, then discovers he’s engaged to the woman whose wedding she’s planning. Professional boundaries and existing relationships apparently don’t stand much of a chance. My Best Friend’s Wedding (1997) Julianne realizes she loves Michael shortly before his wedding and launches a campaign to sabotage his relationship. Thankfully, the movie doesn’t actually reward her behavior with the groom. While You Were Sleeping (1995) Lucy lets a comatose stranger’s family believe they’re engaged, then starts falling for his brother. It’s difficult to imagine explaining that particular misunderstanding at future family gatherings. She’s All That (1999) Zack bets he can transform unpopular Laney into prom queen, pretending to be interested in her along the way. Discovering your relationship started as a wager isn’t exactly romantic. 50 First Dates (2004) Henry pursues Lucy despite her short-term memory loss, meaning she repeatedly has to learn who he is. The romance is sweet, but the practical implications are enormous. You’ve Got Mail (1998) Joe knows his anonymous online crush is Kathleen, the woman whose business his bookstore has threatened. He keeps the secret while pursuing her, which makes their adorable emails considerably messier. Overboard (1987) Dean convinces a wealthy woman with amnesia that she’s his wife, then puts her to work caring for his children. The film somehow expects romance to emerge from this elaborate deception. Failure to Launch (2006) Tripp’s parents hire Paula to date their adult son and persuade him to move out. Finding out your girlfriend was secretly employed by your parents seems like a reasonable dealbreaker. The Ugly Truth (2009) Mike spends much of the movie offering Abby crude dating advice and criticizing her romantic expectations. Naturally, the film eventually decides this is the guy she should fall for. What Women Want (2000) Nick suddenly gains the ability to hear women’s thoughts and uses it to get ahead at work, including stealing ideas from Darcy, the woman he eventually falls for. The post 15 Romcoms Where We Aren’t Exactly Comfortable With the Relationship appeared first on Den of Geek .

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