Movies Like Definitely, Maybe (2008)

Definitely, Maybe is a 2008 comedy, romance film from Adam Brooks with a MovieMagicScore of 6.9/10. Here are 20 similar films, ranked by real viewer ratings — starting with Down to You and What's Your Number?.

Comedy Romance

Down to You

2000

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.

5.2

MagicScore

What's Your Number?

2011

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.

6.5

MagicScore

Friends with Money

2006

As she reaches her mid-thirties and quits her lucrative job, singleton Olivia finds herself unsure about her future and her relationships with her successful and wealthy friends. She begins to envy the security of her richer friends and, although their lives may seem easier, Olivia's friends have their problems too: screenwriters Christine and Patrick are unable to collaborate on their latest project, Jane and Aaron have lost the romance in their relationship, and Franny and Matt have difficulties handling the demands of parenthood.

5.1

MagicScore

What a Girl Wants

2003

An American girl, Daphne, heads to Europe in search of the father she's never met. But instead of finding a British version of her bohemian mother, she learns the love of her mom's life is an uptight politician. The only problem now is that her long-lost dad is engaged to a fiercely territorial social climber with a daughter who makes Daphne's life miserable.

6.3

MagicScore

Unforgettable

2017

Barely coping with the end of her marriage, Tessa Connover learns that her ex-husband, David, is now happily engaged to Julia. Trying to settle into her new life after moving in with David, Julia believes she has finally met the man of her dreams, the man who can help her forget her troubled past. Soon, Tessa's jealousy starts to consume her, and she will stop at nothing to turn Julia's paradise into the ultimate nightmare.

5.9

MagicScore

The Party

1980

A thirteen-year-old French girl deals with moving to a new city and school in Paris, while at the same time her parents are getting a divorce.

6.6

MagicScore

The Party 2

1982

A young French teenage girl after moving to a new city falls in love with a boy and is thinking of having sex with him because her girlfriends have already done it.

6.4

MagicScore

The Legend of Paul and Paula

1973

Paul and Paula have had bad experiences with love: Paul is financially well off but has lost all affection for his wife, and Paula leads a troublesome life raising two children on her own. They meet and discover a strong passion for each other. Life seems like a dream when they're together - but their short flights from the burdens of reality are once and again interrupted by Paul's ties to family and career.

5.8

MagicScore

Just Remembering

2022

A former couple remembers their most intimate days, only to part once again. A bittersweet love story inspired by a Jim Jarmusch masterpiece, set in times of the COVID-19 pandemic.

6.8

MagicScore

#10

The Matchmaker

1997

Marcy, a worker in the reelection campaign of bumbling Senator John McGlory, is sent to Ireland on a quest to find the Irish ancestry of Sen. McGlory, to help him win the Irish vote. But when Marcy arrives in the small village of Ballinagra, she finds herself in the middle of a matchmaking festival, and the local matchmaker is determined to pair her off with one of the local bachelors.

6.2

MagicScore

#11

High Fidelity

2000

After his long-time girlfriend dumps him, a thirty-year-old record store owner seeks to understand why he is unlucky in love while recounting his "top five breakups of all time".

7.1

MagicScore

#12

Dark Horse

2005

A young man spurs romance and helps his friend and himself go through the struggles of their ordinary life in Denmark.

6.7

MagicScore

#13

Frances Ferguson

2019

Frances Ferguson is discontent. Like a lot of us, she does a bit of “acting out” and pays the price —an arrest, a trial, incarceration. And then a new identity, one that’s not terribly comfortable.

6.0

MagicScore

#14

Shall We Kiss?

2007

When Gabriel and Emilie meet by chance, he offers her a ride, and they spend the evening talking, laughing and getting along famously. At the end of the night, Emilie declines Gabriel's offer of "a kiss without consequences". Emilie admonishes him that the kiss could have unexpected consequences, and tells him a story, unfolding in flashbacks, about the impossibility of indulging your desires without affecting someone else's life.

6.1

MagicScore

#15

Notting Hill

1999

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.

7.3

MagicScore

#16

Blind Dating

2006

Danny is a blind man who does not let his impairment get in the way of living his life to the fullest, except when it comes to love. Danny's brother sets him up on a series of blind dates, but all of them go disastrously wrong. Just when Danny is about to give up, he meets Leeza, a nurse who works for Danny's doctor. There is just one catch: Leeza, who is from India, is promised to another man.

6.0

MagicScore

#17

The 10 Year Plan

2014

Myles and Brody are best friends with two very different ways of finding love. Displeased with their current love lives, they make a pact to be together if neither finds love in ten year’s time. Now two months shy of their deadline, both friends set off to do whatever it takes to avoid ending up as each other’s last resort.

6.8

MagicScore

#18

Brown Sugar

2002

Sidney and Dre can attribute their lifelong friendship and the launch of their careers to one single childhood instant... witnessing the birth of hip-hop on a New York street corner. Now some 15 years later, she is a revered music critic at a national magazine and he is a successful, though unfulfilled, hip-hop record company executive. Both come to realize that their true life passions will only be fulfilled by remembering what they learned that day on the corner.

6.6

MagicScore

#19

About Last Night

2014

Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to navigate the relationship minefields from the bar to the bedroom and are eventually put to the test in the real world.

6.0

MagicScore

#20

Stolen

2012

Master thief Will Montgomery is just released from the State penitentiary after serving a 10 year sentence, is contacted by Vincent, his ex comrade in crime, who is holding Will’s teenage daughter ransom in a hijacked taxi cab. Vincent will only surrender her when Will reveals the whereabouts of the 20 million dollars he contrived to conceal from their last robbery.

5.5

MagicScore

Frequently asked

What are the best movies like Definitely, Maybe?

The top films similar to Definitely, Maybe by MovieMagicScore are Down to You (5.2), What's Your Number? (6.5), Friends with Money (5.1). Each shares comedy/romance themes and is ranked by real viewer ratings, not critics or studios.

Is Definitely, Maybe worth watching?

Definitely, Maybe holds a MovieMagicScore of 6.9/10 from 2,540 viewer ratings.

What kind of movie is Definitely, Maybe?

Definitely, Maybe (2008) is a comedy, romance film directed by Adam Brooks, starring Ryan Reynolds, Abigail Breslin, Elizabeth Banks.

Where can I find more recommendations like Definitely, Maybe?

Browse the full ranked list above, or explore more comedy recommendations on MovieMagicScore, where every list is ordered by genuine viewer ratings.

Keep exploring

Movies like Down to You Movies like What's Your Number?Movies like Friends with Money Movies like What a Girl Wants Movies like Unforgettable Movies like The Party

About movies like Definitely, Maybe

This ranked list pairs Definitely, Maybe (2008), a comedy and romance film from Adam Brooks, with similar titles by genre, theme and cast overlap (fans of Ryan Reynolds take note). Unlike critic-driven sites, every position here is ordered by MovieMagicScore — a rating built only from real viewers, with no studio marketing or paid placement. Scores update as more people rate, so the list stays current.

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