Ted, There’s Something About Mary
1 / 10VIEW ALL
He’s supposed to be the quintessential nice guy in this movie, but let’s not forget he hires a private detective to track down a girl he went on a date with 13 years ago. The girl chooses him in the end, though in reality, she’d probably opt for a bodyguard instead.
Duckie, Pretty in Pink
2 / 10VIEW ALL
Say the name “Duckie” to any woman old enough to have seen Pretty in Pink and chances are you’ll be met with “Awww!” Duckie’s earnest love for Andie endears him to many, but how many of us want a lovesick guy who spends most nights riding his bike around our houses and breaking into the back office of the record store where we work? Cute on film, but terrifying in real life.
Lloyd, Say Anything
3 / 10VIEW ALL
Lloyd is one of the most attentive, selfless boyfriends ever, but he also doesn’t know when to take no for an answer. When someone breaks your heart, it’s common to listen to “your songs” on repeat in the privacy of your room. It’s far creepier to play the song you had sex to so loudly and publicly it wakes up the heartbreaker’s dad, too.
Christina, The Sweetest Thing
4 / 10VIEW ALL
Cameron Diaz goes from stalked (in There’s Something About Mary) to stalker in this movie. Her character, Christina, meets a guy at a club and decides he’s worth pursuing. Being a romantic comedy, this means going on a road trip and showing up uninvited at his brother’s wedding. This movie proves that desperation doesn’t look hot on anybody, even Ms. Diaz.
5 / 10VIEW ALL
This was one of my favorite movies as a kid and it’s a wonder I turned out relatively stable (relationship-wise, anyway). Talk about scary—this guy builds mannequins and then falls in love with one. His commitment to her runs so deep that he stands outside a shop window in the pouring rain and calls her his greatest creation. A plastic doll. Yeah …
Lucy, While You Were Sleeping
6 / 10VIEW ALL
Lucy’s character starts off innocent enough, but then she somehow manages to fake an engagement to a guy in a coma she has the hots for, but has never spoken to. She convinces his family (and even the guy once he wakes up!) of their love and finagles her way into their lives. Then it all takes a turn for the better/even more disturbing when she ends up marrying his brother instead. Don’t people usually get arrested for this sort of thing?
Edward, Pretty Woman
7 / 10VIEW ALL
My favorite part of this movie is when Edward takes Vivian shopping—who wouldn’t want an all expenses paid shopping trip in Beverly Hills? But then my friend pointed out the fact that he’s basically playing dress-up with a hooker and Richard Gere never looked the same to me. As if renting a prostitute for a week isn’t strange enough.
Rob, High Fidelity
8 / 10VIEW ALL
Though by no means a standard romantic comedy, this movie does utilize the genre’s oft-celebrated “boy loses girl, boy wins girl back” plot. And true to romantic comedy form, the leading guy’s actions are highly worrisome. He stands outside one ex-girlfriend’s house and yells at her while she’s in the bedroom with her new guy. Later, he calls another ex-girlfriend from a pay phone outside of her new guy’s place. Women need to stop giving their forwarding addresses.
Elle, Legally Blonde
9 / 10VIEW ALL
If a guy dumps you because he thinks you’re not good enough for him, it’s best to say “Good riddance!” and move on. Instead of this sane choice, Elle opts to follow her ex to Harvard Law School in a last-ditch attempt to win him back. Because moving across the country to be in close proximity with the person who doesn’t want you around anymore is as surefire a way as any to make him love you again, right?
Ben, The Graduate
10 / 10VIEW ALL
In the book, Surviving a Stalker, the author, Linden Gross, puts it perfectly: “The Graduate … teaches that if you stay with it, even if you offend a woman, even if she says she wants nothing to do with you, even if you’ve treated her like trash … even if she’s in another relationship, you’ll eventually get the girl.” Ben sleeps with his girl’s mother and ruins her wedding and she still gets on a bus with him. After all that, he could’ve at least picked her up in a car. (Yeah, yeah, his car ran out of gas. Not the point.)