35 Movies to Watch If You Like Crazy, Stupid, Love. (2011)

Friends with Benefits earns its place here by exploring modern dating complications and romantic entanglements with a humorous, contemporary approach. Its witty banter and lively chemistry between characters provide an entertaining take on love and relationships in the modern world.

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 8,461 people. The movie made an estimated total of $149,500,000 in the box office.

The 40 Year Old Virgin features a protagonist struggling to re-enter the dating scene, making it relevant to those interested in personal transformation after romantic setbacks. The film's comedic style and endearing awkwardness deliver both laughs and warmth.

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 7,338 people. The movie made an estimated total of $177,400,000 in the box office.

Definitely, Maybe distinguishes itself through its layered storytelling about relationships and self-discovery. The film invites viewers to unravel a romantic mystery, keeping things engaging while offering a heartfelt look at love across life’s stages.

When Will decides to tell his daughter the story of how he met her mother, he discovers that a second look at the past might also give him a second chance at the future. Definitely, Maybe is a movie from United States of America in English, with a total 1h 52m runtime, released in 2008 with an average rating of 6.9 by 2,658 people. The movie made an estimated total of $55,447,968 in the box office.

It's Complicated fits this list by examining the unpredictable nature of love later in life and the challenges of starting over. This film balances humor with mature relationships, making it both relatable and delightful in its portrayal of romance.

Ten years after their divorce, Jane and Jake Adler unite for their son's college graduation and unexpectedly end up sleeping together. But Jake is married, and Jane is embarking on a new romance with her architect. Now, she has to sort out her life—just when she thought she had it all figured out. It's Complicated is a movie from United States of America in English, with a total 2h 1m runtime, released in 2009 with an average rating of 6.5 by 1,545 people. The movie made an estimated total of $219,103,655 in the box office.

The Big Sick finds its connection through heartfelt depictions of complex relationships tested by unexpected challenges. Audiences will appreciate its emotional honesty, sharp wit, and the way it finds warmth amid adversity.

Pakistan-born comedian Kumail Nanjiani and grad student Emily Gardner fall in love but struggle as their cultures clash. When Emily contracts a mysterious illness, Kumail finds himself forced to face her feisty parents, his family's expectations, and his true feelings. The Big Sick is a movie from United States of America in English, with a total 2h 0m runtime, released in 2017 with an average rating of 7.3 by 2,668 people. The movie made an estimated total of $56,303,596 in the box office.

Forgetting Sarah Marshall is included due to its comedic exploration of bouncing back from heartbreak. The film offers a lighthearted yet sincere portrayal of recovery and personal growth, set against a vibrant backdrop that adds to its appeal.

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 3,749 people. The movie made an estimated total of $105,173,115 in the box office.

About Time brings a unique element through its gentle drama and romance, delving into the personal lessons love teaches over time. Its thoughtful narrative and emotional resonance create a feel-good viewing experience with depth.

The night after another unsatisfactory New Year's party, Tim's father reveals to him that the men in their family have the ability to travel through time. They can't change history, but they can change what happens and has happened in their own lives. Thus begins the start of a lesson in learning to appreciate life itself as it is, as it comes, and most importantly, the people living alongside us. About Time is a movie from United Kingdom in English, with a total 2h 3m runtime, released in 2013 with an average rating of 7.9 by 9,396 people. The movie made an estimated total of $87,100,449 in the box office.

Celeste & Jesse Forever stands out for its nuanced portrayal of relationships transitioning from love to friendship. The emotional complexities and authenticity make it a rewarding watch for anyone interested in the messiness of modern romance.

Celeste and Jesse met in high school and got married young. They laugh at the same jokes and finish each other’s sentences. They are forever linked in their friends’ minds as the perfect couple – she, a high-powered businesswoman and budding novelist; he, a free spirit who keeps things from getting boring. Their only problem is that they have decided to get divorced. Can their perfect relationship withstand this minor setback? Celeste & Jesse Forever is a movie from United States of America in English, with a total 1h 31m runtime, released in 2012 with an average rating of 6.4 by 506 people. The movie made an estimated total of $3,094,813 in the box office.

The Kids Are All Right belongs here through its thoughtful examination of family, relationship dynamics, and evolving love. With touching moments and humor, it paints a compelling picture of commitment and change.

Two women, Nic and Jules, brought a son and daughter into the world through artificial insemination. When one of their children reaches age, both kids go behind their mothers' backs to meet with the donor. Life becomes so much more interesting when the father, two mothers and children start to become attached to each other. The Kids Are All Right is a movie from United States of America in English, with a total 1h 46m runtime, released in 2010 with an average rating of 6.6 by 1,611 people. The movie made an estimated total of $34,705,850 in the box office.

No Strings Attached fits the recommendations thanks to its playful approach to unconventional arrangements between characters. The film’s energetic tone and charm result in an amusing, light exploration of intimacy and expectation.

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 5,039 people. The movie made an estimated total of $149,200,000 in the box office.

Love, Simon finds common ground by spotlighting heartfelt journeys of personal realization and authentic connection. What makes it memorable is its uplifting message and relatable characters navigating young love with sincerity.

Everyone deserves a great love story, but for 17-year-old Simon Spier, it's a little more complicated. He hasn't told his family or friends that he's gay, and he doesn't know the identity of the anonymous classmate that he's fallen for online. Love, Simon is a movie from United States of America in English, with a total 1h 50m runtime, released in 2018 with an average rating of 8.0 by 6,301 people. The movie made an estimated total of $66,316,289 in the box office.

Begin Again earns placement through its uplifting depiction of rebuilding life and love after setbacks. The fusion of music and personal revival creates a feel-good atmosphere that is both hopeful and entertaining.

Gretta, a budding songwriter, finds herself alone after her boyfriend Dave ditches her. Her life gains purpose when Dan, a record label executive, notices her talent. Begin Again is a movie from United States of America in English, with a total 1h 44m runtime, released in 2014 with an average rating of 7.2 by 4,039 people. The movie made an estimated total of $63,500,000 in the box office.

Dan in Real Life is included for its focus on navigating family, heartbreak, and unexpected romance. The story delivers warmth and humor through well-drawn characters and genuine emotional moments.

Advice columnist Dan Burns is an expert on relationships, but somehow struggles to succeed as a brother, a son and a single parent to three precocious daughters. Things get even more complicated when Dan finds out that the woman he falls in love with is actually his brother's new girlfriend. Dan in Real Life is a movie from United States of America in English, with a total 1h 38m runtime, released in 2007 with an average rating of 6.6 by 1,374 people. The movie made an estimated total of $68,474,305 in the box office.

Enough Said draws its relevance from how it examines the intricacies of starting anew in love during midlife. Its subtle humor and realistic character dynamics ensure an experience both comforting and insightful.

Eva is a divorced soon-to-be empty-nester wondering about her next act. Then she meets Marianne, the embodiment of her perfect self. Armed with a restored outlook on being middle-aged and single, Eva decides to take a chance on her new love interest Albert — a sweet, funny and like-minded man. But things get complicated when Eva discovers that Albert is in fact the dreaded ex–husband of Marianne... Enough Said is a movie from United States of America in English, with a total 1h 33m runtime, released in 2013 with an average rating of 6.7 by 931 people. The movie made an estimated total of $25,288,872 in the box office.

Silver Linings Playbook explores the emotional upheaval that romantic transitions can provoke, similar to Crazy, Stupid, Love. The combination of strong performances and an uplifting trajectory makes this film resonate long after the credits roll.

After losing his job and wife, and spending time in an institution, a former teacher winds up living with his parents. He wants to rebuild his life and reconcile with his wife, but his father would be happy if he shared his obsession with the Philadelphia Eagles. Things get complicated when he meets Tiffany Maxwell who offers to help him reconnect with his wife if he will do something very important for her in exchange. Silver Linings Playbook is a movie from United States of America in English, with a total 2h 2m runtime, released in 2012 with an average rating of 7.2 by 12,749 people. The movie made an estimated total of $236,412,453 in the box office.

The Break-Up carves its place in this lineup by addressing the fallout of a long-term relationship in a comedic light. The film balances sharp dialogue and realistic conflict to create a refreshing look at moving on.

Pushed to the breaking-up point after their latest 'why can't you do this one little thing for me?' argument, Brooke calls it quits with her boyfriend Gary. What follows is a hilarious series of remedies, war tactics, overtures and undermining tricks – all encouraged by the former couple's friends and confidantes …and the occasional total stranger! When neither ex is willing to move out of their shared apartment, the only solution is to continue living as hostile roommates until one of them reaches breaking point. The Break-Up is a movie from United States of America in English, with a total 1h 46m runtime, released in 2006 with an average rating of 5.9 by 2,874 people. The movie made an estimated total of $205,700,000 in the box office.

Love Actually is highlighted for its interwoven storytelling, capturing varied perspectives on love and connection. The ensemble cast and feel-good tone make it particularly rewarding for viewers who appreciate complex relationship tapestries.

Eight very different couples deal with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London. Love Actually is a movie from United Kingdom in English, with a total 2h 15m runtime, released in 2003 with an average rating of 7.1 by 7,480 people. The movie made an estimated total of $250,779,876 in the box office.

Don Jon appears on this page due to its exploration of changing perspectives on romance and intimacy. The film's direct style and distinct point of view invite audiences to reconsider preconceived notions about connection.

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 4,632 people.

The Spectacular Now is notable for its honest portrayal of young romance and self-discovery. It draws viewers into a believable coming-of-age journey, underpinned by nuanced emotion and realistic storytelling.

Sutter, a popular party animal, unexpectedly meets the introverted Aimee after waking up on a stranger's lawn. As Sutter deals with the problems in his life and Aimee plans for her future beyond school, an unexpected romance blossoms between them. The Spectacular Now is a movie from United States of America in English, with a total 1h 35m runtime, released in 2013 with an average rating of 6.7 by 3,054 people. The movie made an estimated total of $6,854,611 in the box office.

Swingers earns inclusion by depicting the ups and downs of post-breakup social life with humor and wit. Its lively script and memorable characters capture the challenges and absurdities of moving forward.

After 6 years together, Mike's girlfriend leaves him, so he travels to LA to be a star. Six months on, he's still not doing very well— so a few of his friends try to reconnect him to the social scene and hopefully help him forget his failed relationship. Swingers is a movie from United States of America in English, with a total 1h 36m runtime, released in 1996 with an average rating of 6.8 by 821 people. The movie made an estimated total of $4,505,922 in the box office.

Your Sister's Sister takes its place thanks to its intimate exploration of complex relationship dynamics and emotional vulnerability. The film’s naturalistic tone and personal interactions keep viewers engaged from start to finish.

Iris invites her friend Jack to stay at her family's island getaway after the death of his brother. At their remote cabin, Jack's drunken encounter with Hannah, Iris' sister, kicks off a revealing stretch of days. Your Sister's Sister is a movie from United States of America in English, with a total 1h 30m runtime, released in 2011 with an average rating of 6.5 by 368 people. The movie made an estimated total of $3,242,802 in the box office.

Morning Glory introduces professional struggles affecting personal life, tying into the broader theme of finding balance amid chaos. Its brisk pacing and bright performances contribute to an enjoyable, spirited experience.

A young and devoted morning television producer is hired as an executive producer on a long-running morning show at a once-prominent but currently failing station in New York City. Eager to keep the show on air, she recruits a former news journalist and anchor who disapproves of co-hosting a show that does not deal with real news stories. Morning Glory is a movie from United States of America in English, with a total 1h 47m runtime, released in 2010 with an average rating of 6.4 by 1,653 people. The movie made an estimated total of $60,040,976 in the box office.

She's Out of My League qualifies for its comedic look at insecurities, attraction, and romantic possibilities. With its playful approach and unexpectedly charming moments, it offers a fun take on love’s unpredictability.

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 2,379 people. The movie made an estimated total of $49,800,000 in the box office.

La La Land appears here for its depiction of modern relationships shaped by ambition and changing dreams. The musical elements combine with heartfelt storytelling to create a visually striking and emotionally resonant film.

Mia, an aspiring actress, serves lattes to movie stars in between auditions and Sebastian, a jazz musician, scrapes by playing cocktail party gigs in dingy bars, but as success mounts they are faced with decisions that begin to fray the fragile fabric of their love affair, and the dreams they worked so hard to maintain in each other threaten to rip them apart. La La Land is a movie from United States of America in English, with a total 2h 9m runtime, released in 2016 with an average rating of 7.9 by 18,305 people. The movie made an estimated total of $509,183,536 in the box office.

The Switch fits through its unconventional approach to romance and friendship. It offers a blend of humor and genuine character moments, providing a fresh perspective on familiar romantic challenges.

Kassie is a smart, fun-loving single woman who, despite her neurotic best friend Wally’s objections, decides it’s time to have a baby – even if it means doing it herself… with a little help from a charming sperm donor. But, unbeknownst to her, Kassie’s plans go awry because of a last-minute switch that isn’t discovered until seven years later… when Wally gets acquainted with Kassie’s cute, though slightly neurotic, son. The Switch is a movie from United States of America in English, with a total 1h 41m runtime, released in 2010 with an average rating of 6.2 by 2,059 people. The movie made an estimated total of $49,830,607 in the box office.

Stuck in Love finds relevance in its multi-generational view of love, highlighting the complexities of relationships within a family. Its balanced mix of drama and lighter moments makes it both touching and engaging.

An acclaimed writer, his ex-wife, and their teenaged children come to terms with the complexities of love in all its forms over the course of one tumultuous year. Stuck in Love is a movie from United States of America in English, with a total 1h 37m runtime, released in 2013 with an average rating of 7.4 by 2,028 people. The movie made an estimated total of $977,671 in the box office.

Long Shot is included for its comedic angle on unlikely romance and personal reinvention. The sharp writing and charismatic leads ensure an experience that’s equal parts fun and heartfelt.

Journalist Fred Flarsky reunites with his childhood crush, Charlotte Field, now one of the most influential women in the world. As she prepares to make a run for the Presidency, Charlotte hires Fred as her speechwriter — much to the dismay of her trusted advisers. Long Shot is a movie from United States of America in English, with a total 2h 5m runtime, released in 2019 with an average rating of 6.7 by 2,925 people.

Sleeping with Other People is present due to its candid, comedic exploration of complicated emotional bonds. The film’s honest approach and fast-paced humor add a refreshing layer to the romantic comedy genre.

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 992 people. The movie made an estimated total of $3,214,116 in the box office.

Happythankyoumoreplease stands out for its intertwined stories about navigating love and friendship in adulthood. The ensemble cast and blend of sincerity and humor create a compelling portrait of contemporary relationships.

Six New Yorkers navigate love, commitment, and adulthood. When struggling novelist Sam takes in an abandoned boy he meets on the subway, his life begins to intertwine with a talented singer who challenges his bachelor ways. Meanwhile, his best friend Annie battles alopecia while torn between two drastically different men, and a long-term couple faces a crossroads that could alter their future together. Happythankyoumoreplease is a movie from United States of America in English, with a total 1h 40m runtime, released in 2011 with an average rating of 6.5 by 309 people. The movie made an estimated total of $853,862 in the box office.

The Intern makes the list by exploring personal renewal and unexpected connections later in life. Its gentle storytelling, coupled with uplifting themes, provides an enjoyable experience about starting over.

70-year-old widower Ben Whittaker has discovered that retirement isn't all it's cracked up to be. Seizing an opportunity to get back in the game, he becomes a senior intern at an online fashion site, founded and run by Jules Ostin. The Intern is a movie from United States of America in English, with a total 2h 1m runtime, released in 2015 with an average rating of 7.2 by 7,421 people. The movie made an estimated total of $194,564,672 in the box office.

Admission justifies its placement thanks to its unique blend of professional stakes and budding romance amid life’s unpredictability. The engaging storyline and relatable characters offer a thoughtful and lighthearted take on finding love and purpose.

Straitlaced Princeton University admissions officer Portia Nathan is caught off-guard when she makes a recruiting visit to an alternative high school overseen by her former classmate, the freewheeling John Pressman. Pressman has surmised that Jeremiah, his gifted yet very unconventional student, might well be the son that Portia secretly gave up for adoption many years ago. Admission is a movie from United States of America in English, with a total 1h 47m runtime, released in 2013 with an average rating of 5.6 by 657 people. The movie made an estimated total of $18,637,201 in the box office.

Liberal Arts takes a thoughtful approach to intergenerational attraction and personal growth, standing out through its introspective tone and relatable narrative. The film’s authenticity and warmth make it an engaging exploration of love and self-discovery.

Newly single, 35, and uninspired by his job, Jesse Fisher worries that his best days are behind him. But no matter how much he buries his head in a book, life keeps pulling Jesse back. When his favorite college professor invites him to campus to speak at his retirement dinner, Jesse jumps at the chance. Liberal Arts is a movie from United States of America in English, with a total 1h 37m runtime, released in 2012 with an average rating of 6.5 by 583 people. The movie made an estimated total of $327,345 in the box office.

How Do You Know is well suited to this list for its portrayal of navigating love triangles and big life decisions. The film’s polished blend of comedy and romance results in a charming, heartfelt journey.

After being cut from the USA softball team and feeling a bit past her prime, Lisa finds herself evaluating her life and in the middle of a love triangle, as a corporate guy in crisis competes with her current, baseball-playing beau. How Do You Know is a movie from United States of America in English, with a total 2h 1m runtime, released in 2010 with an average rating of 5.3 by 1,067 people. The movie made an estimated total of $48,668,907 in the box office.

Friends with Kids is included for its exploration of unconventional relationships and how friendship can evolve into something deeper. The sharp humor and ensemble cast deliver a relatable and entertaining perspective on modern love and parenting.

In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other. Friends with Kids is a movie from United States of America in English, with a total 1h 40m runtime, released in 2012 with an average rating of 5.9 by 496 people. The movie made an estimated total of $12,186,625 in the box office.

In Good Company finds common ground with the source film by examining life transitions, both professionally and personally, in a comedic yet sincere manner. Its blend of corporate satire and emotional depth creates a rewarding watch.

Dan Foreman is a seasoned advertisement sales executive at a high-ranking publication when a corporate takeover results in him being placed under naive supervisor Carter Duryea, who is half his age. Matters are made worse when Dan's new supervisor becomes romantically involved with his daughter an 18 year-old college student Alex. In Good Company is a movie from United States of America in English, with a total 1h 50m runtime, released in 2004 with an average rating of 6.1 by 698 people. The movie made an estimated total of $61,314,565 in the box office.