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Home›Best of the Best Lists›10 Best Rom-Coms Where the Guy Falls in Love First

10 Best Rom-Coms Where the Guy Falls in Love First

By Matthew Lynch
March 20, 2024
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Romantic comedies, affectionately known as rom-coms, hold a special place in the hearts of moviegoers. While many stories revolve around women falling head over heels, there’s a delightful charm in narratives where the guy is the first to tumble into love’s deep end. Here’s a roundup of the 10 best rom-coms where the men are struck by cupid’s arrow first.

1.”10 Things I Hate About You” (1999) –This modern retelling of Shakespeare’s ‘The Taming of the Shrew’ shows high school bad boy Patrick Verona falling for the sharp-tongued Kat Stratford. His transformation from initially pursuing her for money to genuinely falling for her is both hilarious and heartwarming.

2.”There’s Something About Mary” (1998) –This Farrelly brothers’ classic has a host of men falling for Cameron Diaz’s Mary, but it’s Ben Stiller’s character Ted who’s been smitten since high school and embarks on a wacky journey to win her heart.

3.”Hitch” (2005) –The date doctor Alex Hitchens, played by Will Smith, is a master at crafting love stories for others but finds himself uncharacteristically floundering when he falls for the gossip columnist Sara Melas.

4.”(500) Days of Summer” (2009) –In this offbeat take on romantic films, hopeless romantic Tom Hansen, portrayed by Joseph Gordon-Levitt, falls hard and fast for Summer Finn, challenging audiences’ ideas about love and fate.

5.”Crazy Stupid Love” (2011) –Steve Carell’s character Cal Weaver navigates newfound singledom, but it’s Ryan Gosling’s suave Jacob Palmer who surprisingly finds himself falling before he even knows what hit him with Emma Stone’s character, Hannah.

6.”Forgetting Sarah Marshall” (2008) –Jason Segel plays Peter Bretter who’s on a Hawaii trip to get over his ex Sarah Marshall, only to realize he’s developing unexpected feelings for Rachel Jansen, played by Mila Kunis.

7.”About Time” (2013) –This British gem involves time travel where Tim Lake (Domhnall Gleeson) uses his special ability to improve his life and falls quickly and deeply for Rachel McAdams’ character Mary.

8.“Notting Hill” (1999) –The quintessential romantic comedy features bookshop owner William Thacker (Hugh Grant) as an ordinary man whose life turns extraordinary when he falls first for famous film star Anna Scott (Julia Roberts).

9.”The Wedding Singer” (1998) –Adam Sandler embodies Robbie Hart, who wears his heart on his sleeve and pines after Drew Barrymore’s Julia Sullivan while helping her plan her wedding.

10.”As Good as It Gets” (1997)– In this dramedy Jack Nicholson plays a grumpy author Melvin Udall who unexpectedly finds himself caring deeply for single mother Carol Connelly played by Helen Hunt.

These films redefine the rom-com playbook by showing that love isn’t just about grand gestures or waiting for someone to notice you—it can start with someone taking that brave first step. Whether it involves time travel or high school hierarchy shakedowns, these movies teach us that when it comes to love, sometimes you have to fall first to find out just how high you can bounce back up.

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