15 Rom-Coms Where The Guy Falls First

Summary

• Modern rom-coms often show the guy falling first, leading to unique and entertaining storylines.
• Rom-com classics featured women seeking love, but newer films showcase more guys falling first.
• Balancing romance and obsession is key in today’s rom-coms where the guy falls first to avoid a troubling narrative.

Romantic comedies have morphed and changed a lot over the years, and rom-coms where the guy falls firstare becoming increasingly common in modern takes on the genre. This is not as unusual a storytelling device as it once was, as it leads to interesting moments where the guy has to work hard to win over his love interest. However, it is also hard because, in today’s society, this is a tightrope the scripts have to walk to ensure that it remains a fun and romantic story, but doesn’t tip over into a more disturbing tale of obsession and pressure from a man who won’t take no for an answer.

For years, the romantic comedies that have stood the test of time often see the woman seeking out the man, putting viewers in her shoes more often than not. Examples include movies from the 80s like Sixteen Candles and Pretty in Pink, where Molly Ringwald plays a high school student who wants to find love and struggles until her dreams come true. Those movies also show guys who seek out their dream girls (Anthony Michael Hall and Jon Cryer, respectively) but fail. Today, movies where the guy falls first are popping up more and more.

15 How To Lose A Guy In 10 Days (2003)

A Man & Woman Hook Up On Two Separate Bets

Matthew McConaughey and Kate Hudson co-star in a romantic comedy about two people who hook up when they set out to prove a point. Hudson’s Andie is a writer for a women’s magazine who tries to prove her place in the magazine by writing a “hot to” article revealing how a woman can lose a man. She sets out to find someone to date and then does everything she can to drive him away. Meanwhile, Ben bets his boss that he can make any woman fall in love with him.

What results is Ben doing everything he can to make Andie fall in love with him, while Andie does everything she can to be annoying, so he will stop dating her.

What results is Ben doing everything he can to make Andie fall in love with him, while Andie does everything she can to be annoying, so he will stop dating her. Things change when Ben starts to see some of Andie’s true sidebehind her annoying persona, and he starts to fall in love with her for real, regardless of his original bet. When Andie finally gives in and falls for Ben, they each learn of the bet/article, throwing a wrinkle into their relationship. The movie was a big box office success and remains a cult classic among rom-coms.

14 Blended (2014)

Two Single Parents Pretend To Be A Couple While On Vacation

What starts as a blind date gone wrong ends up so much worse (and somehow better) when Lauren (Drew Barrymore) and Jim (Adam Sandler) meet again when they learn they’ve both purchased one-half of a South African vacation package for their kids. Now, the two single parents must pretend to be a happy-blended family to save the vacation. Unfortunately, realizing he’s in love with Lauren is only half the battle, because he is a widower and his kids are still grieving, while Lauren’s ex-husband is causing problems.

The movie struggled to make a dent at the box office thanks to the increased diminishing returns of Adam Sandler’s films at the time. Even re-teaming with Drew Barrymore, his romantic interest from the extremely popular The Wedding Singer, the movie was a box office flop, and it earned Sandler and Barrymore Razzie nominations. However, looking back on the movie, it remains a funny romantic comedy and the audience score is much higher than the critics’ score, at 64% on Rotten Tomatoes.

13 Forgetting Sarah Marshall (2008)

A Guy Finds New Love After A Terrible Breakup

After his girlfriend of five years unexpectedly breaks up with him, Peter (Jason Segel) decides to book a Hawaiian vacation to get away. However, getting over her proves difficult when Peter’s ex (Kristen Bell) ends up on the same Hawaiian vacation with her new boyfriend (Russell Brand). Forgetting Sarah Marshall is an interesting movie where the guy falls first because Peter ends up falling for Rachel (Mila Kunis), who works at the resort.

Forgetting Sarah Marshall
was successful enough that it warranted a spinoff movie with
Get Him to the Greek
, with Russell Brand and Jonah Hill returning to their roles.

It is also ironic, since he fell in love with his ex, Sarah, first when they started dating. Thus, it’s clear that Peter wants to find love, even if the women he chases don’t always reciprocate. The movie was a big hit when it came out, with a relatively high (for a romantic comedy) Rotten Tomatoes score of 83% from critics. Kristen Bell won Best Actress at the Teen Choice Awards, and Forgetting Sarah Marshall was successful enough that it warranted a spinoff movie with Get Him to the Greek, with Russell Brand and Jonah Hill returning to their roles.

12 Holidate (2020)

Two Single People Agree To Date During The Holidays

Tired of being the only single person at holiday parties with friends and family, Sloane (Emma Roberts) decides to take a page from her aunt’s book and find herself a “Holidate” (a person who poses as a boyfriend or girlfriend during the holidays). She meets Jackson (Luke Bracey) at the mall while returning unwanted Christmas gifts, and the two end up agreeing to spend New Year’s Eve together, so they won’t be alone. After a successful NYE, they commit to being each other’s plus ones for every holiday that year.

While Sloane and Jackson end up falling for each other, Jackson falls first, and he falls hard. Jackson falls so hard that he tries to push Sloane away, believing she deserves better than him. The two later pause their deal, breaking Jackson’s heart, but it is all worth it when Sloane pulls off a giant Christmas romantic gesture to win him over. This romantic comedy is a Netflix original and ended up as one of the most streamed titles on the streaming giant in 2020 (via Variety).

11 Something Borrowed (2011)

A Woman Sleeps With Her Best Friend’s Fiancé

Something Borrowed centers on Rachel (Ginnifer Goodwin), a chronically single woman who sleeps with her best friend’s fiancé after a night of heavy drinking. He also happens to be her longtime crush. As the wedding planning continues, Rachel grapples with her complicated feelings surrounding the wedding. What’s interesting about Something Borrowed is the guy who falls first isn’t the one anyone suspects.

Despite the poor critical reviews and lower box office totals, a sequel has been in the works since 2014.

Rachel’s best friend and confidant, Ethan (John Krasinski), is the one who ends up admitting that he’s been hopelessly in lovewith her forever, while Dax (Colin Egglesfield) carries on with his plans to marry Rachel’s best friend. The rom-com received overwhelmingly negative critical reviews, sitting at 15% on Rotten Tomatoes, although fans liked it better, with an audience score of 48%. Despite the poor critical reviews and lower box office totals, a sequel has been in the works since 2014.

10 How To Be Single (2016)

An Anthology Series Of Female-Centric Romance

How To Be Single is an anthology rom-com, following the lives of several characters as they navigate relationships in their young lives while living in the city. One of the most underrated stories in the movie is the relationship between hopeless romantic Lucy (Alison Brie) and anti-love bar owner Tom (Anders Holm). The two couldn’t be more opposite. Yet, they form a friendship after Lucy starts frequenting the bar to use its free Wi-Fi, as she uses it to access a dating site to find “the one.”

Soon, anti-love Tom begins to have feelings for Lucy, which is the last thing he ever expected. Watching him pine for her as she gets into other relationships is heartbreaking and wonderful at the same time. The movie struggled at the box office and received mixed-to-low reviews from critics. It did pick up fan support, as it ended up nominated for the Favorite Comedic Movie Award, although it lost out to this hilarious and raunchy R-rated comedy, Bad Moms.

9 Palm Springs (2020)

A Woman Is Trapped In a Time Loop With A Guy Who Has Been There For A Long Time

One of 2020’s biggest romantic comedies was Palm Springs, which was also one of the best time loop movies ever. Nyles (Andy Samberg) has been stuck in a time loop for a long time and after a post-wedding hook-up gone wrong, Sarah (Cristin Milioti) ends up stuck with him. As the two try to make sense of their new reality and get out, Nyles falls in love with Sarah. In fact, he had been in love with her long before she got stuck in the time loop as he interacted with her time and time again, which he revealed during an argument.

The time loop rom-com was also a critical success, earning two Golden Globe nominations

Palm Springs premiered at the Sundance Film Festival and dropped on Hulu the same day it got a limited theatrical release in 2020. The time loop rom-com was also a critical success, earning two Golden Globe nominations, including one for Best Motion Picture – Musical or Comedy and an acting nomination for Andy Samberg. It sits at a very high 94% positive rating on Rotten Tomatoes, with critics comparing it positively to Groundhog Day.

8 Pitch Perfect (2012)

Two Acapella Singers Find Love In College

While Pitch Perfect might be considered more of a musical comedy than a rom-com, it has all the qualities of rom-com. At the center of the movie’s love story is Beca (Anna Kendrick), a rebellious college freshman, and Jesse (Skylar Astin), a fellow freshman. There’s no denying that Jesse experiences love at first sight when he sees Beca moving into her dorm on the first day of school. Jesse continues to pursue Beca, first as a friend, as they work together and eventually become rivals in the acapella world.

And while Beca is the one who makes the grand romantic gesture, it’s Jesse who falls for her first. The movie was a massive hit, making $115 million on a $17 million budget. It also won several awards from the Teen Choice Awards and MTV Movie Awards and spawned its own franchise. A sequel arrived in 2015 and a third movie in 2017 before Peacock brought it back as a streaming series in 2021 with Adam DeVine as the connector to the original cast.

7 Set It Up (2018)

Two Assistants Try To Set Up Their Bosses But Fall In Love

Set It Up is arguably one of Netflix’s most underrated romantic comedies on the streaming service. While there are two love stories at the center of this movie about two assistants setting up their overbearing bosses, it’s the love story involving the assistants that remains the best. Harper (Zoey Deutch) and Charlie (Glen Powell) may not get off on the right foot, but that doesn’t stop a friendship from blossoming. And the more scheming they do together, the more Charlie realizes how amazing Harper is.

Set It Up
was smartly written and proves that even tropes work well when done right

The Netflix release was universally acclaimed by critics, who certified it fresh with a 92% rating on Rotten Tomatoes. While critics pointed out that the movie was full of familiar rom-com tropes, Set It Up was smartly written and proves that even tropes work well when done right, even all these years later. While there is no sequel, director Claire Scanlon said that she has plenty of ideas and viewers can get even more fun scenes on Netflix, as the service released a blooper reel to go with the movie.

6 The Royal Treatment (2022)

A Royal Prince Falls In Love WIth A Hairstylist

The Royal Treatment follows Isabella (Laura Marano), a struggling hairstylist who gets roped into styling the royal wedding of Prince Thomas (Mena Massoud). Like all good rom-coms, this one is extremely cliché, playing into the enemies-to-lovers trope. However, it’s Prince Thomas who falls hopelessly in love despite the fact he’s supposed to marry someone else. Prince Thomas is immediately infatuated with Isabella and learns to love her more when he witnesses her explore parts of his kingdom he hasn’t even ventured into himself.

The movie shows that Isabella’s giant heart has him questioning his entire life and ultimately pulling off a cute grand gesture in the end. The movie, shot in New Zealand with a large local cast, didn’t receive good reviews, but that didn’t stop it from reaching its audience. The movie sat in the number one spot on Netflix the week it was released (via Otago Daily Times), and it offers an unexpectedly fun rom-com experience.

5 To All The Boys I’ve Loved Before (2018)

A High School Girl Has All Her Crushes Made Public

Based on the best-selling teen novel of the same name, To All The Boys I’ve Loved Before is credited for reigniting the teen rom-com genre, especially on Netflix. Fake dating always leads to someone getting real feeling. In this case, it’s Peter (Noah Centineo) who falls first. Some might argue that he’s always had a crush on Lara Jean (Lana Condor), which is why he’s the one who comes up with the fake dating plot in the first place.

Peter’s infatuation makes
To All The Boys I’ve Loved Before
an excellent example of romantic movies where the guy falls first.

Whether it’s driving her and her sister home or making sure he packs all her favorite snacks, Peter’s infatuation makes To All The Boys I’ve Loved Before an excellent example of romantic movies where the guy falls first. The movie was a huge success, with a certified fresh 96% rating on Rotten Tomatoes. It also started a franchise, with two sequels, hitting Netflix in 2020 and 2021. While they didn’t receive as much acclaim, they were still critically accepted and it remains a great trilogy for rom-com fans. There was also a spinoff television series in 2021 called XO, Kitty.

4 What If (2013)

A Classic Friends-To-Lovers Story

After a series of disastrous relationships, Wallace (Daniel Radcliffe) decides to give up on love altogether. However, his plans are quickly thwarted when he meets and bonds with Chantry (Zoe Kazan). The only problem is, Chantry is in a committed relationship. It’s obvious Wallace is the one to fall first in What If, considering Chantry is in a relationship, but that doesn’t make it any less entertaining. He pines for her so hard, and it’s gut-wrenching to watch Chantry carry on with her relationship when the right boyfriend is right in front of her.

The movie was originally called The F Word, but the MPAA demanded a change to get a PG-13 rating. The movie kept the original title outside of the United States and received critical acclaim, named one of the top 10 Canadian movies of the year at the Toronto International Film Festival. It also won the Canadian Screen Award for Best Adapted Screenplay for 2014 and is a perfect example of Daniel Radcliff’s acting outside of period pieces.

3 10 Things I Hate About You (1999)

A Teenage Rom-Com Based On Shakespeare

10 Things I Hate About You is loosely based on Shakespeare’s The Taming of the Shrew. The movie centers on Cameron (Joseph Gordon-Levitt), a new student who wants to date Bianca (Larisa Olyynik), but he learns her dad won’t let her date until her older sister starts dating. This is Kat (Julia Stiles), an abrasive teenager, and Cameron and Bianco try to set her up with Patrick (Heath Ledger), who they pay to go out with Kat. However, Patrick starts to fall for her, but Kat is so blinded by her past relationships that she can’t see how perfect Patrick is for her.

A great look at Heath Ledger as he turned into one of Hollywood’s best young actors.

The movie was a decent box office success, making $60.4 million on a $13 million budget, and it is a great look at Heath Ledger as he turned into one of Hollywood’s best young actors. Gordon-Levitt, Stiles, and Oleynik all received Young Star Award nominations, and the movie also earned nominations at the Teen Choice and MTV Movie Awards. It also spawned a TV show in 2008, which aired for one season on ABC Family.

2 50 First Dates (2004)

A Man Has To Make A Woman Fall In Love With Him Anew Every Day

50 First Dates is one of Adam Sandler’s best romantic comedies and certainly one of the best between him and Drew Barrymore. The movie centers on Henry (Sandler), a playboy marine biologist, who falls for Lucy (Barrymore), a local who experiences short-term memory loss. Even without Lucy’s memory issues, it’s clear that Henry is the one who fell first and fell hard. He immediately seeks her out the next day after meeting her and isn’t even afraid when he learns the truth.

It’s adorable to watch how patient he is with Lucy as she learns to fall in love with him each day.

It’s adorable to watch how patient he is with Lucy as she learns to fall in love with him each day. This was the second collaboration between Sandler and Barrymore, after The Wedding Singer but before Blended. Critics gave the movie mixed to poor reviews, but at a time when Adam Sandler was falling out of favor, that was expected. In reality, the movie remains a popular rom-com and one of Sandler’s better releases, with audiences giving it a better reception at 65% on Rotten Tomatoes.

1 500 Days Of Summer (2009)

A Man Has To Deal With A Woman Falling Out Of Love With Him

500 Days of Summer is one of the most divisive romantic comedies out there, with many claiming it’s an anti-rom-com. The cult classic centers onTom (Joseph Gordon-Levitt) who is head over heels in love with Summer (Zooey Deschanel). While the movie is a textbook example of what’s wrong with the “manic pixie dream girl” character, the truth is it is a rom-com where the guy falls first. In fact, Tom falls so hard when Summer breaks up with him that he doesn’t know what to do with his life.

Tom takes the breakup so hard that he becomes obsessive, and his controlling nature pushes Summer away from him.

This is one rom-com where the guy falls first which shows the toxicity of that idea when it goes to the extreme. Tom takes the breakup so hard that he becomes obsessive, and his controlling nature pushes Summer away from him. Tom takes it one step further and ruins future dates by only talking about Summer to his dates. While Summer tries to remain friends, Tom can’t do so and the former hopeless romantic decides that true love does not exist. The movie finished on several best-of lists for 2009 and won the Independent Spirit Award for Best Screenplay.