31 Best Movies Like Definitely Maybe ...

31 Best Movies Like Definitely Maybe ...

If you liked this one , you will definitely love these too! In this selection we highlight some of the best films that share a very similar premise to '', and are worth checking out.

1. 500 Days of Summer (2009)

1h 35m Comedy Drama Romance

Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.

2. Love, Rosie (2014)

1h 42m Comedy Romance

Since the moment they met at age 5, Rosie and Alex have been best friends, facing the highs and lows of growing up side by side. A fleeting shared moment, one missed opportunity, and the decisions that follow send their lives in completely different directions. As each navigates the complexities of life, love, and everything in between, they always find their way back to each other - but is it just friendship, or something more?

3. The Proposal (2009)

1h 48m Comedy Romance Drama

When she learns she's in danger of losing her visa status and being deported, overbearing book editor Margaret Tate forces her put-upon assistant, Andrew Paxton, to marry her.

4. A Lot Like Love (2005)

1h 47m Comedy Drama Romance

On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to ... lovers?

5. How to Lose a Guy in 10 Days (2003)

1h 56m Comedy Romance

It’s the battle of wills, as Andie (Kate Hudson) needs to prove she can dump a guy in 10 days, whereas Ben (Matthew McConaughey) needs to prove he can win a girl in 10 days. Now, the clock is ticking - and the wildly entertaining comedy smash is off and running in this irresistible tale of sex, lies and outrageous romantic fireworks!

6. Jersey Girl (2004)

1h 42m Comedy Romance Drama

Ollie Trinke is a young, suave music publicist who seems to have it all, with a new wife and a baby on the way. But life deals him a bum hand when he's suddenly faced with single fatherhood, a defunct career and having to move in with his father. To bounce back, it takes a new love and the courage instilled in him by his daughter.

7. Dan in Real Life (2007)

1h 38m Comedy Romance Drama

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.

8. No Reservations (2007)

1h 44m Comedy Romance Drama

Master chef Kate Armstrong runs her life and her kitchen with intimidating intensity. However, a recipe for disaster may be in the works when she becomes the guardian of her young niece while crossing forks with the brash sous-chef who just joined her staff. Though romance blooms in the face of rivalry, Kate needs to look outside the kitchen to find true happiness.

9. The Holiday (2006)

2h 16m Comedy Romance

Two women, one from the United States and one from the United Kingdom, swap homes at Christmastime after bad breakups with their boyfriends. Each woman finds romance with a local man but realizes that the imminent return home may end the relationship.

10. Something's Gotta Give (2003)

2h 8m Drama Comedy Romance

Harry Sanborn is an aged music industry exec with a fondness for younger women like Marin, his latest trophy girlfriend. Things get a little awkward when Harry suffers a heart attack at the home of Marin's mother, Erica. Left in the care of Erica and his doctor, a love triangle starts to take shape.

11. He&`s Just Not That Into You (2009)

12. Sleeping with Other People (2015)

1h 40m Comedy

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.

13. French Kiss (1995)

1h 51m Comedy Romance

After her fiancee admits to infidelity while on a business trip in France, a woman attempts to get her lover back and marry him by traveling to Paris despite her crippling fear of flying. On the way she unwittingly smuggles something of value that has a charming crook chasing her across France as she chases after her future husband.

14. P.S. I Love You (2007)

2h 6m Drama Romance

A young widow discovers that her late husband has left her 10 messages intended to help ease her pain and start a new life.

15. Maid in Manhattan (2002)

1h 45m Comedy Drama Romance

Marisa Ventura is a struggling single mom who works at a posh Manhattan hotel and dreams of a better life for her and her young son. One fateful day, hotel guest and senatorial candidate Christopher Marshall meets Marisa and mistakes her for a wealthy socialite. After an enchanting evening together, the two fall madly in love. But when Marisa's true identity is revealed, issues of class and social status threaten to separate them. Can two people from very different worlds overcome their differences and live happily ever after?

16. Love Actually (2003)

2h 15m Comedy Romance Drama

'Love Actually' follows the lives of eight very different couples dealing with their love lives, in various loosely and interrelated tales, all set during a frantic month before Christmas in London, England.

17. Just Friends (2005)

1h 36m Comedy Romance

While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into a ferocious womanizer.

18. The Back-up Plan (2010)

1h 46m Comedy Romance

When Zoe tires of looking for Mr. Right, she decides to have a baby on her own. But on the day she's artificially inseminated, she meets Stan, who seems to be just who she's been searching for all her life. Now, Zoe has to figure out how to make her two life's dreams fit with each other.

19. The Nanny Diaries (2007)

1h 46m Comedy Drama Romance

A college graduate goes to work as a nanny for a rich New York family. Ensconced in their home, she has to juggle their dysfunction, a new romance, and the spoiled brat in her charge.

20. Enough Said (2013)

1h 33m Comedy Drama Romance

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...

21. Rumor Has It... (2005)

1h 37m Comedy

Sarah Huttinger's return home with her fiance convinces her that the sedate, proper, country-club lifestyle of her family isn't for her – and that maybe the Huttinger family isn't even hers – as she uncovers secrets that suggest the Huttingers are neither sedate nor proper.

22. I Could Never Be Your Woman (2007)

1h 37m Comedy Drama Romance

This movie follows a mother who falls for a younger man while her daughter falls in love for the first time. Mother Nature messes with their fates.

23. In Her Shoes (2005)

2h 10m Comedy Drama Romance

Irresponsible party girl, Maggie is kicked out of her father's and stepmother's home—where she lives for free—and is taken in by her hard-working sister, Philadelphia lawyer, Rose. After Maggie's disruptive ways ruin her sister's love life, Rose turns her out as well. But when their grandmother, who they never knew existed, comes into their lives, the sisters face some complicated truths about themselves and their family.

24. What to Expect When You're Expecting (2012)

1h 50m Romance Comedy Drama

Challenges of impending parenthood turn the lives of five couples upside down. Two celebrities are unprepared for the surprise demands of pregnancy; hormones wreak havoc on a baby-crazy author, while her husband tries not to be outdone by his father, who's expecting twins with his young trophy wife; a photographer's husband isn't sure about his wife's adoption plans; a one-time hook-up results in a surprise pregnancy for rival food-truck owners.

25. Under the Tuscan Sun (2003)

1h 53m Romance Comedy

After a rough divorce, Frances, a 35 year old book editor from San Francisco takes a tour of Tuscany at the urgings of her friends. On a whim she buys Bramasole, a run down villa in the Tuscan countryside and begins to piece her life together starting with the villa and finds that life sometimes has unexpected ways of giving her everything she wanted.

26. When Harry Met Sally... (1989)

1h 36m Comedy Romance Drama

During their travel from Chicago to New York, Harry and Sally debate whether or not sex ruins a friendship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

27. 50 First Dates (2004)

1h 39m Comedy Romance

Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.

28. In Good Company (2004)

1h 49m Comedy Drama Romance

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.

29. The Other Sister (1999)

2h 10m Comedy Drama Romance

A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.

30. How to Be Single (2016)

1h 50m Comedy Romance

New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.

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