Best Movies Like 40 Days and 40 Nights for Fans of Wild Romantic Comedy

Like 40 Days and 40 Nights, this raunchy rom-com turns sexual frustration into a full comedy engine, following a sweet but awkward man pressured by friends into changing his love life.

Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers: Andy is still a virgin. Determined to help Andy get laid, the guys make it their mission to de-virginize him. But it all seems hopeless until Andy meets small business owner Trish, a single mom. The 40 Year Old Virgin is a movie from United States of America in English, with a total 1h 56m runtime, released in 2005 with an average rating of 6.4 by 7,236 people. The movie made an estimated total of $177,400,000 in the box office.

This fits the same early-2000s adult comedy lane, mixing dirty jokes, messy dating, and friendship-driven chaos with a surprisingly romantic center.

Christina's love life is stuck in neutral. After years of avoiding the hazards of a meaningful relationship, one night while club-hopping with her girlfriends, she meets Peter, her perfect match. Fed up with playing games, she finally gets the courage to let her guard down and follow her heart, only to discover that Peter has suddenly left town. Accompanied by Courtney, she sets out to capture the one that got away. The Sweetest Thing is a movie from United States of America in English, with a total 1h 24m runtime, released in 2002 with an average rating of 5.6 by 1,183 people. The movie made an estimated total of $68,696,770 in the box office.

Good Luck Chuck shares the same sex-curse energy as 40 Days and 40 Nights, using an outrageous romantic premise to explore commitment, temptation, and bad dating luck.

Cursed since childhood, dentist Charlie Logan cannot find the right woman. Even worse, he learns that each of his ex-girlfriends finds true love with the man she meets after her relationship with him ends. Hearing of Charlie's reputation as a good-luck charm, women from all over line up for a quick tryst. But when Charlie meets the woman of his dreams, he must find a way to break the curse or risk losing her to the next man she meets. Good Luck Chuck is a movie from Canada in English, with a total 1h 41m runtime, released in 2007 with an average rating of 5.9 by 1,663 people. The movie made an estimated total of $59,768,495 in the box office.

This is a great match for fans of casual-sex rom-coms, where two attractive leads try to avoid feelings until romance complicates the whole arrangement.

Emma is a busy doctor who sets up a seemingly perfect arrangement when she offers her best friend Adam a relationship with one rule: No strings attached. But when a fling becomes a thing, can sex friends stay best friends? No Strings Attached is a movie from United States of America in English, with a total 1h 47m runtime, released in 2011 with an average rating of 6.3 by 4,995 people. The movie made an estimated total of $149,200,000 in the box office.

Friends with Benefits mirrors the playful, sexy tension of 40 Days and 40 Nights, turning a no-strings setup into a battle between lust, rules, and real feelings.

Dylan is done with relationships. Jamie decides to stop buying into the Hollywood clichés of true love. When the two become friends they decide to try something new and take advantage of their mutual attraction - but without any emotional attachment. Friends with Benefits is a movie from United States of America in English, with a total 1h 49m runtime, released in 2011 with an average rating of 6.6 by 8,396 people. The movie made an estimated total of $149,500,000 in the box office.

Zack and Miri Make a Porno fits through its bold sexual premise, awkward intimacy, and friends-to-lovers romance wrapped in crude but oddly heartfelt comedy.

Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each other than they previously thought. Zack and Miri Make a Porno is a movie from United States of America in English, with a total 1h 42m runtime, released in 2008 with an average rating of 6.3 by 2,670 people. The movie made an estimated total of $42,105,111 in the box office.

American Pie delivers the same teen-to-adult raunchy humor, with sexual anxiety, embarrassing mistakes, and friendship at the heart of the comedy.

At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to all "score" by their senior prom. American Pie is a movie from United States of America in English, with a total 1h 35m runtime, released in 1999 with an average rating of 6.6 by 8,321 people. The movie made an estimated total of $235,483,004 in the box office.

The Girl Next Door matches the fantasy-meets-romance feel, mixing sexual temptation, young love, and chaotic comedy around one very unforgettable relationship.

Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds Danielle was once a porn star. As Danielle's past catches up with her, Matthew's love for her forces him to re-evaluate his goals. The Girl Next Door is a movie from United States of America in English, with a total 1h 50m runtime, released in 2004 with an average rating of 6.7 by 4,030 people. The movie made an estimated total of $31,635,150 in the box office.

EuroTrip leans harder into wild travel comedy, but its horny misunderstandings, dating mishaps, and early-2000s energy make it a natural companion pick.

When Scott learns that his longtime cyber-buddy from Berlin is a gorgeous young woman, he and his friends embark on a trip across Europe. EuroTrip is a movie from United States of America in English, with a total 1h 32m runtime, released in 2004 with an average rating of 6.6 by 2,966 people. The movie made an estimated total of $22,605,153 in the box office.

Road Trip fits for its outrageous college humor, sexual panic, and relationship mistakes, giving fans of 40 Days and 40 Nights another chaotic rom-com ride.

After a student at the University of Ithaca films his one-night stand with a beautiful sorority girl, he discovers one of his friends has accidentally mailed the homemade sex tape to his girlfriend in Austin. In a frenzy, he must borrow a car and hit the road in a desperate bid to intercept the tape. Road Trip is a movie from United States of America in English, with a total 1h 33m runtime, released in 2000 with an average rating of 6.2 by 2,191 people. The movie made an estimated total of $119,754,278 in the box office.

Sex Drive shares the same obsession with desire, awkward romance, and ridiculous obstacles, making it a fast, crude, and funny match for the topic.

A high school senior drives cross-country with his best friends to hook up with a babe he met online. Sex Drive is a movie from United States of America in English, with a total 1h 49m runtime, released in 2008 with an average rating of 6.4 by 1,478 people. The movie made an estimated total of $18,755,936 in the box office.

This rom-com fits through its insecure hero, unbelievable romance, and constant tension between attraction, self-doubt, and what friends think.

When he starts dating drop-dead gorgeous Molly, insecure airport security agent Kirk can't believe it. As his friends and family share their doubts about the relationship lasting, Kirk does everything he can to avoid losing Molly forever. She's Out of My League is a movie from United States of America in English, with a total 1h 44m runtime, released in 2010 with an average rating of 6.5 by 2,337 people. The movie made an estimated total of $49,800,000 in the box office.

Just Friends brings messy romantic timing, old crushes, and comic embarrassment, making it a strong pick for viewers who liked the awkward heart of 40 Days and 40 Nights.

While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into a ferocious womanizer. Just Friends is a movie from United States of America in English, with a total 1h 34m runtime, released in 2005 with an average rating of 6.2 by 1,802 people. The movie made an estimated total of $50,817,508 in the box office.

How to Lose a Guy in 10 Days works because it also builds romance around a ridiculous dating challenge, with two leads slowly falling for each other despite the rules.

It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and running in this irresistible tale of sex, lies and outrageous romantic fireworks! How to Lose a Guy in 10 Days is a movie from United States of America in English, with a total 1h 56m runtime, released in 2003 with an average rating of 6.9 by 4,482 people. The movie made an estimated total of $177,500,000 in the box office.

Just Married matches the same early-2000s rom-com flavor, with attractive leads, romantic chaos, and a relationship tested by one disaster after another.

Although Tom Leezak and Sarah McNerney come from different worlds, they are both unexpectedly swept off their feet after their first meeting. They quickly fall in love and plan to get married, despite opposition from Sarah's uptight, rich family. After their wedding, the happy couple sets off - with the highest of hopes and ideals about love and marriage - on what they expect will be the perfect honeymoon in Italy. Thanks to a relentless string of bad luck with one disaster after another, and an impromptu visit from Sarah's wealthy one-time ex-lover Peter Prentiss, the newlyweds experience the honeymoon from hell that tests the limits of their young love. Is it worth throwing away their love and marriage? Just Married is a movie from United States of America in English, with a total 1h 35m runtime, released in 2003 with an average rating of 5.8 by 1,462 people. The movie made an estimated total of $101,564,935 in the box office.

What Women Want fits through its battle-of-the-sexes comedy, workplace romance, and playful focus on attraction, misunderstanding, and emotional growth.

Advertising executive Nick Marshall is as cocky as they come, but what happens to a chauvinistic guy when he can suddenly hear what women are thinking? Nick gets passed over for a promotion, but after an accident enables him to hear women's thoughts, he puts his newfound talent to work against Darcy, his new boss, who seems to be infatuated with him. What Women Want is a movie from United States of America in English, with a total 2h 7m runtime, released in 2000 with an average rating of 6.5 by 4,382 people. The movie made an estimated total of $374,100,000 in the box office.

Hitch is a smoother romantic comedy, but its dating lessons, romantic panic, and big-hearted approach make it a good match for fans of messy love stories.

Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships. Hitch is a movie from United States of America in English, with a total 1h 58m runtime, released in 2005 with an average rating of 6.6 by 6,231 people. The movie made an estimated total of $371,600,000 in the box office.

Forgetting Sarah Marshall connects through breakup pain, sexual awkwardness, and a hero trying to rebuild himself while romance sneaks up on him.

When actress Sarah Marshall dumps aspiring musician Peter Bretter for rock star Aldous Snow, Peter's world comes crashing down. His best friend Brian suggests that Peter should get away from everything and to fly off to Hawaii to escape all his problems. After arriving in Hawaii and meeting the beautiful receptionist Rachel Jansen, Peter is shocked to see not only Aldous in Hawaii, but also Sarah. Forgetting Sarah Marshall is a movie from United States of America in English, with a total 1h 51m runtime, released in 2008 with an average rating of 6.5 by 3,698 people. The movie made an estimated total of $105,173,115 in the box office.

Knocked Up shares the same adult rom-com DNA, turning casual sex, panic, and emotional immaturity into a funny story about growing up for love.

A slacker and a career-driven woman accidentally conceive a child after a one-night stand. As they try to make the relationship work, they must navigate the challenges of parenthood and their differences in lifestyle and maturity. Knocked Up is a movie from United States of America in English, with a total 2h 9m runtime, released in 2007 with an average rating of 6.3 by 4,291 people. The movie made an estimated total of $219,900,000 in the box office.

Wedding Crashers fits the same raunchy romantic comedy zone, where bad behavior, temptation, and unexpected love collide in loud, crowd-pleasing fashion.

John and his buddy Jeremy are emotional criminals who know how to use a woman's hopes and dreams for their own carnal gain. Their modus operandi: crashing weddings. Normally, they meet guests who want to toast the romantic day with a random hook-up. But when John meets Claire, he discovers what true love – and heartache – feels like. Wedding Crashers is a movie from United States of America in English, with a total 1h 59m runtime, released in 2005 with an average rating of 6.5 by 4,712 people. The movie made an estimated total of $288,500,000 in the box office.

There's Something About Mary is a key pick for fans of sexual embarrassment, romantic obsession, and outrageous comedy built around one unforgettable woman.

For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy detective he hired to find her. There's Something About Mary is a movie from United States of America in English, with a total 2h 0m runtime, released in 1998 with an average rating of 6.6 by 5,358 people. The movie made an estimated total of $369,900,000 in the box office.

Down to You has a similar young-love focus, following attraction, breakup pain, and romantic confusion with a late-90s and early-2000s dating vibe.

College coeds in New York City, Al, the son of a celebrity chef, and Imogen, a talented artist, become smitten the second they lay eyes on one another at a bar. However, the road to happiness is not a smooth one. Outside forces, including a predatory porn star who wants to lure Al into her bed, threaten to pull apart the young lovers before their romance has a chance to really flourish. Down to You is a movie from United States of America in English, with a total 1h 31m runtime, released in 2000 with an average rating of 5.2 by 264 people.

Loser fits through its awkward college romance, shy leading man, and sweet outsider energy, offering a softer companion to 40 Days and 40 Nights.

On a university scholarship, a good natured student from the midwest gets a crash course in city life while dealing with three evil roommates. He befriends a virtually homeless college student whom he falls for, but she's dating a nasty professor. Loser is a movie from United States of America in English, with a total 1h 35m runtime, released in 2000 with an average rating of 5.4 by 481 people.

100 Girls shares the same sexually curious comedy spirit, using a mystery-romance setup filled with campus crushes, desire, and youthful confusion.

Matthew, a college freshman, meets his dream girl in a dorm elevator during a blackout. He never sees her face, but instantly falls in love. In the morning, the power is restored, but the "dream girl" has vanished. All Matthew knows is that she lives in an all-girls dorm. He sets out on a semester-long journey to find his mystery girl among a hundred female suspects. Could it be Wendy? Dora? Arlene? Patty? Cynthia? Or the 95 other girls, any of whom could have been in that elevator with Matthew. 100 Girls is a movie from United States of America in English, with a total 1h 35m runtime, released in 2000 with an average rating of 5.7 by 487 people.

Boys and Girls fits the topic with its friends-to-lovers story, college-age romance, and comic tension between friendship, attraction, and bad timing.

Ryan and Jennifer are opposites who definitely do not attract. At least that's what they always believed. When they met as twelve-year-olds, they disliked one another. When they met again as teenagers, they loathed each other. But when they meet in college, the uptight Ryan and the free-spirited Jennifer find that their differences bind them together and a rare friendship develops. Boys and Girls is a movie from United States of America in English, with a total 1h 34m runtime, released in 2000 with an average rating of 6.0 by 426 people. The movie made an estimated total of $20,627,372 in the box office.

National Lampoon's Van Wilder brings the same early-2000s party-comedy mood, with flirtation, immaturity, and romance hiding beneath the raunch.

Van Wilder has been attending college for far too many years and is scared to graduate, but Van’s father eventually realizes what is going on. When he stops paying his son's tuition fees, Van must come up with the money if he wants to stay in college, so he and his friends come up with a great fund-raising idea – throwing parties. However, when the college magazine finds out and reporter Gwen is sent to do a story on Van Wilder, things get a little complicated. National Lampoon's Van Wilder is a movie from United States of America in English, with a total 1h 32m runtime, released in 2002 with an average rating of 6.0 by 1,954 people. The movie made an estimated total of $39,241,323 in the box office.

Slackers matches through its campus setting, crude humor, and tangled romantic schemes, making it a fitting pick for fans of wild dating comedies.

Dave, Sam and Jeff are about to graduate from Holden University with honors in lying, cheating and scheming. The three roommates have proudly scammed their way through the last four years of college and now, during final exams, these big-men-on-campus are about to be busted by the most unlikely dude in school. Self-dubbed Cool Ethan, an ambitious nerd with a bad crush, enters their lives one day and everything begins to unravel. Slackers is a movie from Canada in English, with a total 1h 26m runtime, released in 2002 with an average rating of 5.2 by 214 people. The movie made an estimated total of $6,413,915 in the box office.

Buying the Cow fits with its nervous approach to commitment, male friendship, and romantic indecision, all wrapped in adult comedy and dating panic.

A commitment-averse man frantically hits the dating scene after his girlfriend starts pressuring him to pop the question. Buying the Cow is a movie from United States of America in English, with a total 1h 28m runtime, released in 2002 with an average rating of 5.1 by 122 people.

Along Came Polly offers awkward romance, post-breakup healing, and opposites-attract chemistry, making it a lighter but relevant match for 40 Days and 40 Nights fans.

Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's world is turned upside down, as he makes an uproarious attempt to change his life from middle-of-the-road to totally-out-there. Along Came Polly is a movie from United States of America in English, with a total 1h 30m runtime, released in 2004 with an average rating of 6.0 by 3,027 people. The movie made an estimated total of $178,300,000 in the box office.

Failure to Launch fits through its arrested-development hero, romantic setup, and comedy about finally growing up enough to handle a real relationship.

At 35, Tripp has an interesting job, a hip car, a passion for sailing, an active dating life, and a great house - trouble is, he still lives with his parents, Al and Sue, who are not happy about it. Al and Sue are fascinated when friends whose adult son has recently moved away from home reveal they hired an expert to help. In desperation to push Tripp out of the nest once and for all, Al and Sue hatch a plan to hire Paula, an "interventionist," who has a formula in these cases. Failure to Launch is a movie from United States of America in English, with a total 1h 37m runtime, released in 2006 with an average rating of 5.8 by 1,798 people. The movie made an estimated total of $130,224,158 in the box office.

The Heartbreak Kid shares the theme of romantic regret and temptation, turning a bad relationship decision into a messy, adult comedy of desire and consequences.

Eddie, the 40-year-old confirmed bachelor finally says "I do" to the beautiful and sexy Lila. But during their honeymoon in Mexico, the woman of his dreams turns out to be a total nightmare, and the guy who could never pull the trigger realizes he’s jumped the gun. The Heartbreak Kid is a movie from United States of America in English, with a total 1h 56m runtime, released in 2007 with an average rating of 5.8 by 1,756 people. The movie made an estimated total of $128,453,183 in the box office.

My Boss's Daughter matches the same broad early-2000s rom-com chaos, with a desperate crush, escalating disasters, and a hero trying too hard to win the girl.

When a young man agrees to housesit for his boss, he thinks it'll be the perfect opportunity to get close to the woman he desperately has a crush on – his boss's daughter. But he doesn't plan on the long line of other houseguests that try to keep him from his mission. And he also has to deal with the daughter's older brother, who's on the run from local drug dealers. My Boss's Daughter is a movie from United States of America in English, with a total 1h 23m runtime, released in 2003 with an average rating of 5.0 by 728 people.

The New Guy fits more as a teen comedy cousin, with reinvention, popularity, flirting, and embarrassing schemes driving the laughs.

Nerdy high school senior Dizzy Harrison has finally gotten lucky -- after purposely getting expelled, he takes lessons in 'badass cool' from a convict and enrolls at a new school. But can he keep up the ruse? The New Guy is a movie from United States of America in English, with a total 1h 28m runtime, released in 2002 with an average rating of 5.9 by 654 people. The movie made an estimated total of $31,200,000 in the box office.

Can't Hardly Wait shares youthful romantic urgency, party chaos, crushes, and one-night emotional stakes that pair well with early-2000s dating comedies.

It's graduation day at Huntington Hills High, and you know what that means - time to party. And not just any party, either. This one will be a night to remember, as the nerds become studs, the jocks are humiliated, and freshman crushes blossom into grown-up romance. Can't Hardly Wait is a movie from United States of America in English, with a total 1h 40m runtime, released in 1998 with an average rating of 6.2 by 590 people. The movie made an estimated total of $25,605,015 in the box office.

Whatever It Takes fits through its teen romance scheming, awkward attraction, and playful focus on people chasing the wrong person before seeing the right one.

A nerdy teen, Ryan Woodman is smitten with the popular and gorgeous Ashley Grant, who apparently has no interest in him. Meanwhile, dim star athlete Chris Campbell has his eye on Ryan's brainy and beautiful friend, Maggie Carter. The two agree to help each other in their romantic quests, but, as they come closer to their goals, both Ryan and Chris suspect that they might be pursuing the wrong girls. Whatever It Takes is a movie from United States of America in English, with a total 1h 34m runtime, released in 2000 with an average rating of 5.8 by 301 people. The movie made an estimated total of $9,902,115 in the box office.

Say It Isn't So brings outrageous romantic complications and gross-out humor, making it a good fit for viewers who want the wilder side of 40 Days and 40 Nights.

Boy meets girl; boy falls in love (and had wild, non-stop sex) with girl; boy loses girl... when they discover they are brother and sister! But when he learns that he's the victim of the ultimate case of mistaken identity, the lovesick young man -- whom everyone still thinks is after some taboo thrills -- must race across the country to stop her from marrying another man. Say It Isn't So is a movie from United States of America in English, with a total 1h 35m runtime, released in 2001 with an average rating of 4.8 by 182 people. The movie made an estimated total of $12,320,393 in the box office.

Deuce Bigalow: Male Gigolo connects through its sex-comedy setup, oddball romance, and jokes built around intimacy, insecurity, and surprising sweetness.

Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer is hot on his trail. Deuce Bigalow: Male Gigolo is a movie from United States of America in English, with a total 1h 28m runtime, released in 1999 with an average rating of 6.0 by 1,542 people. The movie made an estimated total of $92,938,755 in the box office.

Tomcats fits the topic with bachelor bets, sex-driven comedy, and immature men learning that love can ruin even the dumbest plans.

College buddies chip in and promise that the group's last unmarried man will collect a cash pot. Seven years later, the kitty is worth $500,000 -- money Michael needs to pay a gambling debt. Problem is, the only other single guy is a hopeless womanizer! Tomcats is a movie from United States of America in English, with a total 1h 35m runtime, released in 2001 with an average rating of 5.1 by 280 people. The movie made an estimated total of $23,400,000 in the box office.

The Ugly Truth matches the battle between romance and sexual honesty, with sharp flirting, dating advice, and heated chemistry at the center.

A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result. The Ugly Truth is a movie from United States of America in English, with a total 1h 36m runtime, released in 2009 with an average rating of 6.5 by 3,778 people. The movie made an estimated total of $321,700,000 in the box office.

Ghosts of Girlfriends Past fits through its womanizing hero, romantic regret, and comic lesson about choosing real love over endless temptation.

Celebrity photographer Connor Mead lives life in the fast lane, committed to lifelong bachelorhood and simultaneous relationships with multiple women. On the eve of his younger brother Paul's wedding, Connor's mockery of love proves a real buzz-kill for everyone - including his childhood crush, Jenny, the one woman who always seemed immune to his considerable charms. Later that night, he gets a wake-up call from the ghost of his late Uncle Wayne, the hard-partying, legendary ladies' man who was Connor's mentor. Uncle Wayne has an urgent message which he delivers through three ghosts who guide Connor on an eye-opening tour of his romantic past, present and future. Along the way, they attempt to discern whether he will ever be able to change his ways -- and if there is any hope of him finding true love. Ghosts of Girlfriends Past is a movie from United States of America in English, with a total 1h 55m runtime, released in 2009 with an average rating of 6.0 by 2,436 people. The movie made an estimated total of $102,366,815 in the box office.

Two Night Stand shares the modern hookup-to-romance path, trapping two strangers in awkward intimacy until jokes, honesty, and attraction take over.

After an extremely regrettable one night stand, two strangers wake up to find themselves snowed in after sleeping through a blizzard that put all of Manhattan on ice. They're now trapped together in a tiny apartment, forced to get to know each other way more than any one night stand should. Two Night Stand is a movie from United States of America in English, with a total 1h 26m runtime, released in 2014 with an average rating of 6.4 by 1,920 people. The movie made an estimated total of $868,081 in the box office.

That Awkward Moment fits through male friendship, commitment panic, and the messy point where casual dating turns into something real.

Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The three young men make a pact to have fun and avoid commitment. However, when all three find themselves involved in serious relationships, they must keep their romances secret from one another. That Awkward Moment is a movie from United States of America in English, with a total 1h 34m runtime, released in 2014 with an average rating of 6.1 by 2,736 people. The movie made an estimated total of $45,600,000 in the box office.

Sleeping with Other People is a sharper modern match for 40 Days and 40 Nights, exploring desire, restraint, friendship, and romantic timing with adult wit.

Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done. Sleeping with Other People is a movie from United States of America in English, with a total 1h 40m runtime, released in 2015 with an average rating of 6.3 by 980 people. The movie made an estimated total of $3,214,116 in the box office.

Trainwreck fits through its commitment-phobic lead, casual-sex comedy, and emotional shift from reckless dating to unexpected romance.

Ever since her father drilled into her head that monogamy isn't realistic, magazine writer Amy has made promiscuity her credo. As much as she enjoys an uninhibited life free of commitment, Amy is really in a rut. While writing a profile about charming and successful sports doctor Aaron Conners, she finds herself actually falling in love for the first time -- and what's more, Aaron seems to really like her too. Amy starts to wonder if it's time to clean up her act and face her fears. Trainwreck is a movie from United States of America in English, with a total 2h 5m runtime, released in 2015 with an average rating of 5.8 by 2,722 people. The movie made an estimated total of $140,795,793 in the box office.

Don Jon connects through its frank look at sex, fantasy, and real intimacy, giving the topic a darker, more self-aware modern edge.

A New Jersey guy dedicated to his family, friends, and church, develops unrealistic expectations from watching porn and works to find happiness and intimacy with his potential true love. Don Jon is a movie from United States of America in English, with a total 1h 30m runtime, released in 2013 with an average rating of 6.0 by 4,582 people.

I Love You, Beth Cooper fits with its crush-fueled chaos, teen wish fulfillment, and one wild night of romantic and comic embarrassment.

A valedictorian's declaration of love for a high-school cheerleader launches a night of revelry, reflection and romance for a group of graduating seniors. I Love You, Beth Cooper is a movie from United States of America in English, with a total 1h 42m runtime, released in 2009 with an average rating of 6.0 by 964 people. The movie made an estimated total of $15,300,000 in the box office.

Nick and Norah's Infinite Playlist offers a sweeter alternative, with one-night romance, post-breakup awkwardness, and the thrill of unexpected chemistry.

Nick cannot stop obsessing over his ex-girlfriend, Tris, until Tris' friend Norah suddenly shows interest in him at a club. Thus begins an odd night filled with ups and downs as the two keep running into Tris and her new boyfriend while searching for Norah's drunken friend, Caroline, with help from Nick's band mates. As the night winds down, the two have to figure out what they want from each other. Nick and Norah's Infinite Playlist is a movie from United States of America in English, with a total 1h 29m runtime, released in 2008 with an average rating of 6.4 by 1,278 people. The movie made an estimated total of $33,600,000 in the box office.

Accepted fits as a youth comedy with rebellion, parties, crushes, and underdog charm, echoing the playful spirit around early-2000s romantic chaos.

A high school slacker who's rejected by every school he applies to opts to create his own institution of higher learning, the South Harmon Institute of Technology, on a rundown piece of property near his hometown. Accepted is a movie from United States of America in English, with a total 1h 33m runtime, released in 2006 with an average rating of 6.4 by 1,786 people. The movie made an estimated total of $38,505,009 in the box office.

Get Over It matches through breakup recovery, teenage romance, and goofy emotional confusion, making it a light fit for fans of dating-centered comedies.

When Berke Landers, a popular high school basketball star, gets dumped by his life-long girlfriend, Allison, he soon begins to lose it. But with the help of his best friend Felix's sister Kelly, he follows his ex into the school's spring musical. Thus ensues a love triangle loosely based upon Shakespeare's "A Midsummer Night's Dream", where Berke is only to find himself getting over Allison and beginning to fall for Kelly. Get Over It is a movie from United States of America in English, with a total 1h 27m runtime, released in 2001 with an average rating of 5.6 by 308 people. The movie made an estimated total of $19,900,366 in the box office.

Splitsville fits the same adult relationship-comedy lane, with modern romance, messy breakups, and the kind of romantic confusion that keeps movies like 40 Days and 40 Nights fun.

After Ashley asks for a divorce, good-natured Carey runs to his friends, Julie and Paul, for support. He’s shocked to discover that the secret to their happiness is an open marriage, that is until Carey crosses the line and throws all of their relationships into chaos. Splitsville is a movie from United States of America in English, with a total 1h 45m runtime, released in 2025 with an average rating of 6.3 by 213 people. The movie made an estimated total of $3,487,610 in the box office.