Definitely, Maybe (2008) is a comedy movie directed by Adam Brooks. The list below collects the movies that people who loved it enjoyed most, best known first.

★ 6.5 · 2,485 votes · Comedy, Romance
Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.
Movies like What's Your Number? →
★ 7.3 · 6,933 votes · Romance, Comedy
London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.
Movies like Notting Hill →
★ 6.6 · 4,138 votes · Comedy, Romance, Drama
Remember that really cute girl/guy who said they'd call – and didn't? Maybe they lost your number. Maybe they're in the hospital. Maybe they're awed by your looks, brains or success. Or maybe... They're just not that into you.

★ 6.8 · 4,897 votes · Mystery, Romance, Sci-Fi
David Aames has it all: wealth, good looks and gorgeous women on his arm. But just as he begins falling for the warmhearted Sofia, his face is horribly disfigured in a car accident. That's just the beginning of his troubles as the lines between illusion and reality, between life and death, are blurred.
Movies like Vanilla Sky →
★ 6.8 · 3,100 votes · Comedy, Drama, Romance
Over the course of five social occasions, a committed bachelor must consider the notion that he may have discovered love.
Movies like Four Weddings and a Funeral →
★ 8.2 · 6,003 votes · Romance, Drama
Seventeen-year-old Stella spends most of her time in the hospital as a cystic fibrosis patient. Her life is full of routines, boundaries and self-control — all of which get put to the test when she meets Will, an impossibly charming teen who has the same illness. There's an instant flirtation, though restrictions dictate that they must maintain a safe distance between them. As their connection intensifies, so does the temptation to throw the rules out the window and embrace that attraction.
Movies like Five Feet Apart →
★ 6.7 · 3,483 votes · Comedy, Drama, Family
Mia Thermopolis is now a college graduate and on her way to Genovia to take up her duties as princess. Accompanied by her friend Lilly, Mia continues her 'princess lessons', like riding horses side-saddle and archery. But her already complicated life is turned upside down once again when she learns that she is to take the crown as queen earlier than expected, all while she meets a mysteriously charming young man.
Movies like The Princess Diaries 2: Royal Engagement →
★ 6.3 · 5,098 votes · Comedy, Romance
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?
Movies like No Strings Attached →
★ 7.2 · 9,223 votes · Drama, Comedy
Lady Bird McPherson, a strong willed, deeply opinionated, artistic 17 year old comes of age in Sacramento. Her relationship with her mother and her upbringing are questioned and tested as she plans to head off to college.
Movies like Lady Bird →
★ 7.9 · 12,734 votes · Comedy, Romance
At a tiny Parisian café, the adorable yet painfully shy Amélie accidentally discovers a gift for helping others. Soon Amelie is spending her days as a matchmaker, guardian angel, and all-around do-gooder. But when she bumps into a handsome stranger, will she find the courage to become the star of her very own love story?
Movies like Amélie →
★ 7.6 · 8,793 votes · Comedy, Romance
Lara Jean's love life goes from imaginary to out of control when her secret letters to every boy she's ever fallen for are mysteriously mailed out.
Movies like To All the Boys I've Loved Before →
★ 6.3 · 587 votes · Comedy
An underachieving vocal coach is motivated by her father, the king of movie-trailer voice-overs, to pursue her aspirations of becoming a voice-over star. Amidst pride, sexism and family dysfunction, she sets out to change the voice of a generation.
Movies like In a World... →
★ 6.6 · 721 votes · Comedy, Romance
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
Movies like Little Italy →
★ 6.5 · 4,572 votes · Comedy, Romance
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.
Movies like What Women Want →
★ 6.5 · 405 votes · Comedy, Romance
Six Californians start a club to discuss the works of Jane Austen. As they delve into Austen's literature, the club members find themselves dealing with life experiences that parallel the themes of the books they are reading.
Movies like The Jane Austen Book Club →
★ 6.5 · 473 votes · Comedy, Romance
A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
Movies like Easy Virtue →
★ 7.6 · 5,184 votes · Comedy, Romance
With college decisions looming, Elle juggles her long-distance romance with Noah, changing relationship with bestie Lee and feelings for a new classmate.
Movies like The Kissing Booth 2 →
★ 7.4 · 9,245 votes · Romance, Comedy
Vivian is a carefree, streetwise diamond in the rough when she meets sophisticated billionaire Edward in a chance encounter that turns into a week-long business arrangement. But Vivian's energetic spirit challenges Edward's no-nonsense approach to life, and soon they are teaching each other – and falling in love!
Movies like Pretty Woman →
★ 6.8 · 925 votes · Comedy, Romance
The balance of power in four couples’ relationships is upset when the women start using the advice in Steve Harvey’s book, Act Like A Lady, Think Like A Man, to get more of what they want from their men. When the men realize that the women have gotten a hold of their relationship “playbook,” they decide that the best defense is a good offense and come up with a plan to use this information to their advantage.
Movies like Think Like a Man →