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

Romantic comedies are typically (and rudely) categorized as “chick flicks” because it is expected that more women than men want to watch characters fall in love while also having a few laughs along the way. The data doesn’t lie when it comes to audience demographics, but that is no reason to poke fun at a genre that leaves fans feeling happy and warm inside.

Looking at standard rom-coms, the plot tends to follow two people who typically get on one another’s nerves (or never before saw the spark between them) go about their business until chemistry arises for the pair to see, and then the rest is history. A conversation that almost always comes up is who is catching or has caught feelings for whom first.

Most times, both individuals make hints that love is in the air in their own respective ways, but they don’t say the three magic words until the end of the movie. Given that the target audience is women, it would make sense for the woman to embrace her stance and make her feelings know first. However, seeing things go the other way where the man admits he is in love first is a great twist.

Here are the 10 best rom-coms where the guy falls in love first.

10 Sweet Home Alabama

Puppy love can be a lot stronger than people think, and when a 10-year-old Jake tells Melanie that he is going to marry her someday to be able to kiss her any time he wants, she should have believed his proposal right then and there. The pair did get married young in Sweet Home Alabama, but they parted ways as Melanie wanted a big life in New York City.

Upon her new engagement, she went back to her hometown to officially divorce Jake, but that is much easier said than done. He refuses to sign the divorce papers for quite some time until he feels like Melanie is no longer the girl he’s pined for all these years. When Melanie does realize her own feelings for her not-so-ex-husband, the two finally embrace and accept one another for who they are.

What Makes It Great

Reese Witherspoon is practically the queen of romantic comedies, and as she stars alongside the Yellowstone actor Josh Lucas, chemistry is immediately in the air. The move-from-a-small-town-to-the-big-city trope is used in the film (like many other rom-coms), but it works because of the past the two share. The film won several awards, one of which included the Teen Choice Award for the Choice Movie Liplock, a scene that happened in a cliché-but-still-perfect way.

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9 50 First Dates

50 First Dates

Release Date

February 13, 2004

Director

Peter Segal

Cast

Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin, Lusia Strus, Dan Aykroyd

Rating

PG-13

Genres

Comedy, Romance

Adam Sandler and Drew Barrymore star in 50 First Dates as Henry, the marine vet at Sea Life Park Hawaii, and Lucy, a woman who experienced a tragic accident just one year prior that left her with short-term memory loss that “resets” every time she goes to sleep. Henry learns that Lucy’s friends and family have been creating the illusion that she’s reliving the same day before her accident over and over again, so she is not in shock and bothered by her reality.

Henry also finds that is he so in love with Lucy that he is willing to go the extra mile and try different tactics to make her reality better and hopefully create a life with her. In the end, Henry has loved Lucy for years, and Lucy experiences the same exciting and “new” love each day she wakes up to Henry and her growing family.

What Makes It Great

Sandler and Barrymore’s chemistry was first seen on the set of The Wedding Singer, and after 50 First Dates, they paired back up for yet another rom-com, Blended. Of the three, as well as just about every other movie Sandler’s done, fans get to see a more tender side to his character. Henry is in love shortly after meeting Lucy, and he has to put in the time, effort, and understanding to pursue the relationship. Though the effects of the amnesia are fictitious, it was a unique element to add to make this film stand out from other romantic comedies.

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8 Holidate

Holidate

Release Date

October 27, 2020

Director

John Whitesell

Cast

Emma Roberts, Frances Fisher, Kristin Chenoweth, Andrew Bachelor, Luke Bracey, Jessica Capshaw

Genres

Comedy, Drama, Romance

Most people can sympathize when it comes to watching a character in a film go through the inevitable stress that comes with the holidays. In Holidate, Sloan is tired of being drilled by her family about always being single during the holidays. At the mall, she meets Jackson, a guy who does not believe in commitment, but is also tired of bad holiday dates.

The pair agree to “date” only on holidays, but after a very vulnerable time together during Halloween, Jackson ends up confessing his feelings for Sloan during the next holiday get-together. She becomes hesitant and defensive, and the pair break off their friendship, only for Sloan to later realize and express her feelings very publicly.

What Makes It Great

Holiday movies are so much fun, and there is a certain magic in the air that comes with them. By creating a single film that deals with the clichés and events only on holidays, along with two stubborn people who are clearly meant to be together, Holidate simply feels like a cozy blanket wrapping up a lot of laughs. Emma Roberts is also very good at playing the annoyed adult daughter who wants to just make it through the festivities, and Luke Bracey complements Roberts’ sass and crude jokes.

Stream on Netflix

7 10 Things I Hate About You

10 Things I Hate About You

Release Date

March 31, 1999

Director

Gil Junger

Cast

Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz

Rating

PG-13

Genres

Comedy, Drama, Romance

There are a few romances to look at throughout the beloved ’90s film, 10 Things I Hate About You, but the one where the guy certainly is the first to fall in love is the one between Cameron (Joseph Gordon-Levitt) and Bianca (Larisa Oleynik). Cameron is the new kid in school, and it is love at first sight the moment he sees Bianca. Cameron and his new friend Michael concoct a plan for him to get close to Bianca, but that involves the school bully, an outcast, and Bianca’s man-eating older sister. As all high school schemes go, things are much easier said than done. In the end Cameron is able to get his feelings across, and everyone except the bully seems to get a happy ending.

What Makes It Great

Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt playing love-struck teenagers in their breakout roles should have anyone excited to see this modern Shakespearean adaptation. The soundtrack is phenomenal, the witty one-liners are hysterical, and the heart-to-heart conversation between the sisters is comforting. Stiles won two awards for her role as the shrew-like older sister, Kat, and Ledger was nominated for his iconic musical performance of “Can’t Take My Eyes Off You”.

Stream on Disney+

Related: The Kings and Queens of ’90s Rom-Coms

6 Love Hard

Love Hard plays on a fear that many people in the technologically advanced dating world have: getting catfished. Natalie has been documenting the bad luck she’s had with her internet dates, but she ends up falling for a guy, Justin Lin, as they have genuine conversations and plenty of late-night phone calls. She makes a surprise trip to Josh’s hometown to meet him, only to find out that he used another man’s picture for his profile.

After the initial frustration, the two create a plan that will satisfy both parties: Josh will introduce Natalie to the man she thought she fell for, and Natalie will pretend to be Josh’s girlfriend for the holidays to fool his parents. What could go wrong? Well, Josh clearly had feelings from the start, but it takes Natalie a while to realize she loves Josh.

What Makes It Great

Fans fell in love with Nina Dobrev as she portrayed Elena Gilbert in TheVampire Diaries, and Jimmy O. Yang has been on the rise for a few years now with his stand-up comedy. Because the circumstances under which the characters meet is such a common situation for people, audiences could easily relate or buy into the storyline. Then, as the two create the plan to benefit both of them, viewers were able to predict the ending, but the holiday festivities and realization between the two young adults was still fun to witness.

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5 Clueless

Clueless

Release Date

July 19, 1995

Director

Amy Heckerling

Cast

Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd, Donald Faison, Elisa Donovan

Rating

PG-13

Genres

Comedy, Documentary, Romance

Romance, comedy, and a glamorized coming-of-age story, what more could anyone ask for? After successfully getting two teachers together in Clueless, Cher Horowitz (Alicia Silverstone) puts herself in charge of selflessly helping people, and her next project is the new girl in school, Tai (Brittany Murphy). While this is going on, and Cher is also scoping out her own love interests, her former step-brother, Josh (Paul Rudd) lingers in the background as he teases her, but also cares about her wellbeing.

We see Josh’s feelings for Cher surface first when he gets jealous of her pursuing something with the new boy at school, but later, after she realizes she is really not his type, Cher reevaluates herself and realizes she also loves Josh.

What Makes It Great

The ’90s were on point when it came to the fashion industry intermingling with teenagers. Silverstone will forever be an icon with her yellow plaid schoolgirl outfit, and seeing Murphy undergo the “geek to glam” transformation that so many rom-coms and coming-of-age films tend to use is humorous and adorable. Silverstone won numerous awards for her breakout role, and the film has been considered a cult classic.

Stream on Paramount+

4 Mamma Mia!

Mamma Mia

Release Date

July 2, 2008

Director

Phyllida Lloyd

Cast

Amanda Seyfried, Stellan Skarsgård, Pierce Brosnan, Nancy Baldwin, Colin Firth, Heather Emmanuel

Rating

PG-13

Genres

Comedy, Musical, Romance

Mamma Mia! is filled with amazing actors, the pursuit of love, and the best songs to which everyone can sing along. Sophie (Amanda Seyfried) sends out wedding invitations to three different men, hoping one will reveal himself as her father, so he can walk her down the aisle at her wedding. When the men show up and see their former love, Donna (Meryl Streep), Sophie’s mother, it is Sam (Pierce Brosnan) who reveals that he still has feelings for her. To make a trip all the way to Greece for a wedding is one thing, but to do it in hopes that chemistry will reignite is quite romantic.

What Makes It Great

The connection between Meryl Streep and Amanda Seyfried as a mother-daughter duo is unmatched. Both women show off their talents as singers in this musical film while expressing that women can and always should support their closest friends even through the chaotic and hard times. While some critics were not so nice when it came to other actors’ singing voices, the overall feeling of this upbeat and catchy film is fun and exciting.

Rent on Prime Video

Related: Mamma Mia! Producer Judy Craymer Says a Third Movie Is In The Works: “It Will Happen”

3 13 Going on 30

13 Going on 30

Release Date

April 13, 2004

Director

Gary Winick

Cast

Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis, Kathy Baker, Phil Reeves

Rating

PG-13

Genres

Comedy, Fantasy, Romance

In 13 Going on 30, Jenna is just 13, but she desperately wants to be popular, and she does not realize that her best friend, Matty, is completely in love with her. After a party fiasco, Jenna jumps forward in time to her “30, flirty, and thriving” years, and she realizes how selfish she has been over the last 17 years.

She has been backstabbing her boss and coworkers, she bailed on Matty, and she does not like who she’s become. When Jenna desperately tries to get her best friend to give their relationship a chance, he respectfully declines as he’s engaged to someone else. All of a sudden, the magic dust from Jenna’s dream house sends her back to her 13th birthday, and she gets a do-over.

What Makes It Great

The overall message of the film is that not everyone receives a second chance when it comes to finding their one true love, so take a look around now to see the amazing people and opportunities in front of you. Seeing Mark Ruffalo as a sweet and considerate character opposite Jenna Gardner is heartwarming as well as humorous.

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2 How to Lose a Guy in 10 Days

How to Lose A Guy In 10 Days

Release Date

February 7, 2003

Director

Donald Petrie

Cast

Kate Hudson, Matthew McConaughey, Kathryn Hahn, Annie Parisse, Adam Goldberg, Thomas Lennon

Rating

PG-13

Genres

Comedy, Romance

Who doesn’t love a little healthy competition when it comes to getting people to fall in love? Andie, a how-to article writer for a women’s magazine in How to Lose a Guy in 10 Days, has a deal with her boss that she can get a guy to fall in and out of love with her as she plans to write her eponymous piece. Ben, an advertisement executive, bets his boss that he can make a woman fall in love with him in 10 days to prove that he knows all about romance.

Of course, as fate and a couple snarky co-workers would have it, these two meet and become the focus for each respective projects without knowing of the other’s intentions. While Andie acts needy and rude at times, Ben actually starts to fall in love with her real personality. After their deals are revealed, it is Ben who chases Andie down to profess his feelings, and she reciprocates and says she has also fallen in love with him.

What Makes It Great

Kate Hudson is a staple when it comes to romantic comedies, and fans like to believe that Matthew McConaughey can get practically any woman to fall in love with him. While the plot is predictable, there is something comforting in knowing how things will end between the two charming and determined characters. The dates they go on, the conversations they have, and the crazy antics are all relatable to a certain degree, but most importantly, they make for a cute and humorous film.

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1 Made of Honor

Made of Honor

Release Date

April 30, 2008

Director

Paul Weiland

Cast

Patrick Dempsey, Michelle Monaghan, Kevin McKidd, Kadeem Hardison, Chris Messina, Richmond Arquette

Rating

PG-13

Genres

Comedy, Romance

Men and women can be best friends, but when a man puts all of his emotional connection into his woman best friend and simply hops from one woman to the next for sex, at some point he will realize who he truly loves, right? In Made of Honor, Tom (Patrick Dempsey) and Hannah (Michelle Monaghan) have been best friends since their senior year of college, and while they do everything together, they have remained only friends. When Hannah leaves for a work-trip to Scotland, Tom realizes his feelings for her, but when she returns, she announces her engagement. Hurt, Tom sets out to be the best “man of honor,” but he also wants to prove that his love for Hannah is enough.

What Makes It Great

Almost everyone can sympathize with the unrequited crush storyline, but watching Dempsey play a character that tries to own up and be the best maid of honor his newly-engaged best friend needs it heartwarming. Of course, audiences are rooting for the cancelation of the spontaneous Scotland wedding the entire time. All Grey’s Anatomy fans will love seeing Owen (Kevin McKidd) and McDreamy (Dempsey) compete with one another in a much different setting.

Stream on STARZ