When it comes to feel-good romantic comedies that leave you with a smile on your face, Crazy, Stupid, Love is hard to beat. This charming 2011 film starring Steve Carell, Ryan Gosling, Julianne Moore and Emma Stone weaves together multiple love stories while deftly balancing humor and heart.
If you adored the witty banter, relatable characters, and intertwining storylines of Crazy, Stupid, Love, you’re probably on the hunt for more movies that deliver the same delightful mix of laughter and romance. Look no further! We’ve compiled a list of the 22 best films to watch next. From modern classics to hidden gems, these picks capture the magic of Crazy, Stupid, Love.
1. When Harry Met Sally (1989)
One of the most iconic romantic comedies of all time, When Harry Met Sally follows the title characters (played by Billy Crystal and Meg Ryan) through 12 years of chance encounters in New York City. Can men and women ever really be “just friends”? This hilarious and heartfelt film seeks to answer that eternal question. With razor-sharp dialogue and unforgettable scenes, it set the template for the modern rom-com.
2. Silver Linings Playbook (2012)
In this quirky, bittersweet love story, Bradley Cooper stars as Pat, a man struggling with bipolar disorder who moves back in with his parents after a stint in a mental institution. He forms an unlikely bond with Tiffany (Jennifer Lawrence), an eccentric young widow. As the two heal from past wounds, they discover an undeniable connection. Tackling mental health issues with sensitivity and humor, Silver Linings Playbook is a refreshingly authentic romantic dramedy.
3. 500 Days of Summer (2009)
500 Days of Summer deconstructs the typical boy-meets-girl formula, instead presenting a realistic and non-linear look at the rise and fall of a relationship. Joseph Gordon-Levitt is Tom, a hopeless romantic who falls hard for Summer (Zooey Deschanel), the new girl at work. But Summer doesn’t believe in love, leading to 500 days of happiness, heartbreak, and everything in between. With a hip soundtrack and inventive storytelling, this indie charmer is perfect for those who appreciate a fresh take on the genre.
4. About Time (2013)
From Richard Curtis, the writer of classics like Four Weddings and a Funeral and Love Actually, comes this sweet, life-affirming romantic comedy with a time-travel twist. When Tim (Domhnall Gleeson) learns the men in his family can travel back in time, he uses his power to win the heart of the lovely but insecure Mary (Rachel McAdams). But Tim soon realizes that his gift can’t shield him from life’s everyday challenges. About Time is a poignant reminder to cherish each moment with the ones we love.
5. Definitely, Maybe (2008)
Will Hayes (Ryan Reynolds) is in the midst of a divorce when his young daughter (Abigail Breslin) asks him to tell the story of how he met her mother. Will recounts his past romances with three women, changing their names so his daughter must guess which one became his wife. As the story unfolds, full of surprising revelations, Will gains a new perspective on his life and loves. Definitely, Maybe is a sweet, nostalgic film about the winding path to finding “the one.”
6. Forgetting Sarah Marshall (2008)
Written by and starring Jason Segel, Forgetting Sarah Marshall follows Peter, a struggling musician who takes a Hawaiian vacation to cope with a devastating breakup from his TV star girlfriend, Sarah (Kristen Bell). But in a hilariously awkward turn of events, Sarah and her new rock star beau are staying at the same resort. As Peter attempts to move on, he finds himself drawn to the hotel’s charming receptionist (Mila Kunis). With a stellar supporting cast and plenty of raunchy humor, this comedy is perfect for fans of Judd Apatow’s signature style.
7. Notting Hill (1999)
In this beloved British rom-com, Hugh Grant stars as William Thacker, a London bookshop owner whose world is turned upside down when he meets Anna Scott (Julia Roberts), a famous American actress. As the two embark on an unlikely romance, they must navigate the challenges of fame and the pressures of their very different lives. With a sharp script and undeniable chemistry between its leads, Notting Hill is a timeless tale of love against the odds.
8. 10 Things I Hate About You (1999)
Loosely based on Shakespeare’s The Taming of the Shrew, this ’90s teen classic stars Julia Stiles as Kat Stratford, an intelligent and rebellious high school senior who wants nothing to do with dating. When Kat’s younger sister is forbidden from dating until Kat has a boyfriend, a plan is hatched to set Kat up with the school’s mysterious bad boy, Patrick Verona (Heath Ledger). With witty dialogue, swoon-worthy romance, and an iconic soundtrack, 10 Things I Hate About You is a must-watch for any rom-com fan.
9. Easy A (2010)
In this smart and sassy teen comedy, Emma Stone stars as Olive, a clean-cut high school student who lies about losing her virginity to boost her social standing. As rumors spread and Olive embraces her new “bad girl” persona, she learns important lessons about reputation, friendship, and staying true to oneself. With sharp social commentary and a star-making turn from Stone, Easy A is a fresh and funny take on the high school rom-com.
10. Groundhog Day (1993)
Bill Murray stars as Phil Connors, a cynical TV weatherman who finds himself stuck in a time loop, forced to relive the same day over and over again in the small town of Punxsutawney, Pennsylvania. As Phil struggles to break free from the endless cycle of February 2nd, he begins to reexamine his life and priorities, ultimately falling for his kind-hearted producer, Rita (Andie MacDowell). Equal parts hilarious and thought-provoking, Groundhog Day is a comedy classic with a philosophical bent.
11. The Big Sick (2017)
Based on the real-life romance of Kumail Nanjiani and Emily V. Gordon, The Big Sick follows Kumail (playing a version of himself), a Pakistani-American comedian who falls for grad student Emily (Zoe Kazan) despite his family’s traditional expectations. When Emily falls gravely ill, Kumail must navigate the medical crisis with her parents, whom he’s never met. Balancing laugh-out-loud humor with poignant cultural insights, The Big Sick is a refreshingly honest and heartfelt love story.
12. Bridget Jones’s Diary (2001)
In this beloved British rom-com based on the novel by Helen Fielding, Renée Zellweger stars as the lovably awkward Bridget Jones, a 32-year-old single woman who resolves to improve her life and find love. Bridget soon finds herself torn between two very different men: her charming boss Daniel (Hugh Grant) and the surly but honorable Mark Darcy (Colin Firth). With relatable mishaps, witty narration, and a stellar cast, Bridget Jones’s Diary is a comfort-watch classic.
13. Knocked Up (2007)
When a one-night stand between slacker Ben (Seth Rogen) and career-driven Alison (Katherine Heigl) results in an unplanned pregnancy, the mismatched pair must navigate the challenges of impending parenthood together. Filled with Judd Apatow’s signature blend of raunchy humor and heartfelt moments, Knocked Up is a hilarious and surprisingly poignant look at love, responsibility, and growing up.
14. Love Actually (2003)
This star-studded British ensemble comedy follows multiple storylines during the holiday season, exploring love in all its forms—from first crushes to longtime marriages. With an A-list cast including Hugh Grant, Emma Thompson, Alan Rickman, and Keira Knightley, Love Actually weaves together both hilarious and heartbreaking moments. It’s a must-watch for anyone who believes in the power of love to overcome even the biggest obstacles.
15. The 40-Year-Old Virgin (2005)
Steve Carell stars as Andy, a kind-hearted but shy electronics store employee who has yet to experience intimate relations at the age of 40. When his coworkers discover his secret, they embark on a mission to help him lose his virginity. But along the way, Andy meets Trish (Catherine Keener), a single mother who challenges him to rethink his priorities. Combining raunchy humor with a surprising sweetness, The 40-Year-Old Virgin is a comedy with heart.
16. Friends with Benefits (2011)
Jamie (Mila Kunis) and Dylan (Justin Timberlake) think it’s going to be easy to add sex to their friendship, despite what Hollywood romantic comedies would have them believe. They soon discover that getting physical always leads to complications. With a clever script and charismatic leads, Friends with Benefits offers a fresh twist on the “sex pact” rom-com formula.
17. Sleeping with Other People (2015)
Jake (Jason Sudeikis) and Lainey (Alison Brie) impulsively lose their virginity to each other in college. When their paths cross twelve years later in New York, they realize they both have become serial cheaters. Bonding over their chronic infidelity, they form a platonic friendship to support each other in their quests for healthy romantic relationships. Sleeping with Other People is a sharp, sexy rom-com that dares to ask the question: can love bloom from a friendship based on sex addiction?
18. Enough Said (2013)
Eva (Julia Louis-Dreyfus), a divorced single parent, spends her days enjoying work as a masseuse but dreading her daughter’s impending departure for college. She meets Albert (James Gandolfini)—a sweet, funny and like-minded man also facing an empty nest. As their romance blossoms, Eva befriends Marianne (Catherine Keener), her new massage client. Marianne is a beautiful poet who seems “almost perfect” except for one prominent quality: she rags on her ex-husband way too much. Enough Said is a charming, bittersweet comedy about facing the doubts of middle-age romance.
19. The Five-Year Engagement (2012)
On their one-year anniversary, sous chef Tom Solomon (Jason Segel) plans to surprise his girlfriend, Violet Barnes (Emily Blunt), with an engagement ring. The lovers do end up engaged, but the fact that the proposal does not go exactly as planned proves to be a harbinger of things to come. Each time they try to set a date, various obstacles stand in their way. The Five-Year Engagement is a funny, poignant look at the pressures of modern romance and career ambitions.
20. What If (2013)
Wallace (Daniel Radcliffe) and Chantry (Zoe Kazan) meet at a party and feel an instant connection, striking up a close friendship. But there’s a problem: Chantry has a serious boyfriend. Wallace, burned by a failed relationship, is wary of falling in love again – especially with someone who’s unavailable. Together, they both attempt the impossible: trying to keep their friendship platonic. What If is a charming, quirky comedy about the eternal question: can men and women really just be friends?
21. Obvious Child (2014)
Brooklyn comedian Donna Stern (Jenny Slate) gets dumped, fired and pregnant just in time for Valentine’s Day. Better off without her unfaithful boyfriend, Donna has a drunken hook-up with a cute, nice guy named Max (Jake Lacy) who wants to date her, but she’s not sure how to tell him she’s pregnant with his child. Obvious Child is a refreshingly honest, hilarious rom-com that doesn’t shy away from the realities of modern love and sex.
22. The Spectacular Now (2013)
Sutter Keely (Miles Teller) lives in the now. A high school senior, charming and self-possessed, he’s the life of the party, loves his job at a men’s clothing store, and has no plans for the future. Then he meets Aimee Finecky (Shailene Woodley), a nice girl who reads science fiction and doesn’t have a boyfriend. While Amy has dreams of a future, Sutter lives in the impressive delusion of a spectacular now, yet somehow, they’re drawn together. The Spectacular Now is a tender, insightful coming-of-age dramedy about an unlikely teen romance.
Whether you’re in the mood for a classic like When Harry Met Sally, a quirky indie like 500 Days of Summer, or a heartfelt comedy like The Big Sick, these 22 films are sure to satisfy your craving for smart, funny, and swoon-worthy romance. Each offers its own unique take on love and relationships while delivering the same irresistible blend of humor and heart that made Crazy, Stupid, Love an instant favorite.
So grab some popcorn, settle in, and get ready to laugh, cry, and fall in love with these unforgettable romantic comedies. From the witty banter to the heartwarming moments, these films remind us of the crazy, stupid, wonderful ways that love can change our lives. Happy watching!
