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Definitely, Maybe poster

Movies that feel likeDefinitely, Maybe (2008)

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.

If you loved Definitely, Maybe, the closest films we have are Zack and Miri Make a Porno (2008), Lisbela and the Prisoner (2003) and Trainwreck (2015). All three share Definitely, Maybe's witty and playful feel, which is what we rank on before quality.

Seen the big three already? The under-the-radar pick below is Obvious Child (2014).

🍅 71% Rotten Tomatoes★ 7.1 IMDb ↗TMDB ↗dir. Adam Brookswittyplayfulromantic
7 of 12 streaming nowNetflix · Amazon Prime Video · Paramount Plus Premium

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If Definitely, Maybe hit the spot, these will too

Zack and Miri Make a Porno poster
Zack and Miri Make a Porno
2008 · dir. Kevin Smith
🍅 65%★ 6.5comedy · romance

Both keep coming back to the same thing: best friend

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.

Lisbela and the Prisoner poster
Lisbela and the Prisoner
2003 · dir. Guel Arraes
★ 7.6comedy · romance

One thread runs through both: romance

Lisbela is a young woman who loves going to the movies. Leléu is a con man, going from town to town selling all sort of things and performing as master of ceremonies for some cheesy numbers, such as the woman who gets transformed into a gorilla. He gets involved with Linaura, a sexy and beautiful woman who happens to be the wife of the most frightening hitman of the place. The hitman finds out his wife's affair and goes after Leléu, who has to leave in a hurry. In another town, he meets and falls instantly in love with Lisbela, who is engaged to Douglas, a hillbilly who tries hard to pass for a cosmopolitan Rio de Janeiro dweller.

Trainwreck poster
Trainwreck
2015 · dir. Judd Apatow
🍅 84%★ 6.2comedy · romance

Both are built on the same subject: falling in love

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.

Long Shot poster
Long Shot
2019 · dir. Jonathan Levine
🍅 82%★ 6.8comedy · romance

Common ground: politics

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.

Obvious Child poster
Obvious Child
2014 · dir. Gillian Robespierre
🍅 90%★ 6.7comedy · romance

Both land wit and play at once

An immature, newly unemployed comic must navigate the murky waters of adulthood after her fling with a graduate student results in an unplanned pregnancy.

My Best Friend's Wedding poster
My Best Friend's Wedding
1997 · dir. P.J. Hogan
🍅 75%★ 6.4comedy · romanceParamount+

Romantic comedy, and it commits to that

When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.

Rich in Love poster
Rich in Love
2020 · dir. Bruno Garotti
★ 6romance · comedyNetflix

The same preoccupation in both: romance

Working incognito at his rich dad's company to test his own merits, Teto falls for Paula and tells her he grew up poor, a lie that spins out of control.

The Ugly Truth poster
The Ugly Truth
2009 · dir. Robert Luketic
🍅 14%★ 6.4comedy · romance

Both keep coming back to the same thing: relationship

The difference: The critics' underdog of the pair

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.

She's Out of My League poster
She's Out of My League
2010 · dir. Jim Field Smith
🍅 57%★ 6.4romance · comedyParamount+

Both keep coming back to the same thing: falling in love

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.

Bridget Jones: The Edge of Reason poster
Bridget Jones: The Edge of Reason
2004 · dir. Beeban Kidron
🍅 27%★ 6comedy · romanceParamount+Starz

Romance built on wit, twice over

Bridget Jones is still dating her new love, barrister Mark Darcy, for a perfect six weeks. However, while on assignment in Thailand with her disreputable ex, Daniel Cleaver, claiming to be reformed, Bridget questions if she has everything she's ever dreamed of having.

No Strings Attached poster
No Strings Attached
2011 · dir. Ivan Reitman
🍅 47%★ 6.2comedy · romance

Both are built on the same subject: parents and children

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?

A Rainy Day in New York poster
A Rainy Day in New York
2019 · dir. Woody Allen
🍅 46%★ 6.4comedy · romancePrime Video

Comedy with a pulse of play, in both cases

Two young people arrive in New York to spend a weekend, but once they arrive they're met with bad weather and a series of adventures.

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The best-reviewed films that share Definitely, Maybe’s defining feeling.