Best movies like Definitely, Maybe

Similar in 86%

In the Land of Women (2007)

Plot Summary:

After a bad breakup with his girlfriend leaves him heartbroken, Carter Webb moves to Michigan to take care of his ailing grandmother. Once there, he gets mixed up in the lives of the mother and daughters who live across the street.

Similar in 79%

In Good Company (2004)

Plot Summary:

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.

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Elizabethtown (2005)

Plot Summary:

Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when he returns to his family's small Kentucky hometown after his father dies. Along the way, he meets a flight attendant with whom he falls in love.

Similar in 79%

Laggies (2014)

Plot Summary:

Overeducated and underemployed, 28 year old Megan is in the throes of a quarterlife crisis. Squarely into adulthood with no career prospects, no particular motivation to think about her future and no one to relate to, Megan is comfortable lagging a few steps behind - while her friends check off milestones and celebrate their new grown-up status. When her high-school sweetheart proposes, Megan panics and- given an unexpected opportunity to escape for a week - hides out in the home of her new friend, 16-year old Annika and Annika's world-weary single dad Craig.

Similar in 79%

Jersey Girl (2004)

Plot Summary:

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.

Similar in 82%

Before Sunrise (1995)

Plot Summary:

On his way to Vienna, American Jesse meets Céline, a student returning to Paris. After long conversations forge a surprising connection between them, Jesse convinces Celine to get off the train with him in Vienna. Since his flight to the U.S. departs the next morning and he has no money for lodging, they wander the city together, taking in the experiences of Vienna and each other.

Similar in 84%

Spanglish (2004)

Plot Summary:

Mexican immigrant and single mother Flor Moreno finds housekeeping work with Deborah and John Clasky, a well-off couple with two children of their own. When Flor admits she can't handle the schedule because of her daughter, Cristina, Deborah decides they should move into the Clasky home. Cultures clash and tensions run high as Flor and the Claskys struggle to share space while raising their children on their own, and very different, terms.

Similar in 81%

A Lot Like Love (2005)

Plot Summary:

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?.

Similar in 84%

The Switch (2010)

Plot Summary:

An unmarried 40-year-old woman turns to a turkey baster in order to become pregnant. Seven years later, she reunites with her best friend, who has been living with a secret: he replaced her preferred sperm sample with his own.

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The Back-up Plan (2010)

Plot Summary:

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.

Similar in 90%

P.S. I Love You (2007)

Plot Summary:

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

Similar in 77%

One Day (2011)

Plot Summary:

A romantic comedy centered on Dexter and Emma, who first meet during their graduation in 1988 and proceed to keep in touch regularly. The film follows what they do on July 15 annually, usually doing something together.

Similar in 79%

New York, I Love You (2008)

Plot Summary:

New York, I Love You delves into the intimate lives of New Yorkers as they grapple with, delight in and search for love. Journey from the Diamond District in the heart of Manhattan, through Chinatown and the Upper East Side, towards the Village, into Tribeca, and Brooklyn as lovers of all ages try to find romance in the Big Apple.

Similar in 87%

Friends with Kids (2011)

Plot Summary:

In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.

Similar in 84%

Dan in Real Life (2007)

Plot Summary:

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.

Similar in 77%

He's Just Not That Into You (2009)

Plot Summary:

Remember that really cute guy who said he'd call – and didn't? Maybe he lost your number. Maybe he's in the hospital. Maybe he's awed by your beauty, brains or success. Or maybe... he's just not that into you.

Similar in 81%

The Nanny Diaries (2007)

Plot Summary:

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.

Similar in 88%

500 Days of Summer (2009)

Plot Summary:

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.

Similar in 89%

Life as We Know It (2010)

Plot Summary:

After a distastrous first date for caterer Holly and network sports director Messer, all they have is common is a dislike for each other and their love for their goddaughter Sophie. But when they suddenly become all Sophie has in this world, Holly and Messer must set their differences aside. Juggling careers and social calendars, they'll have to find common ground while living under the same roof.

Similar in 86%

No Reservations (2007)

Plot Summary:

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.

Similar in 77%

Love Actually (2003)

Plot Summary:

Follows seemingly unrelated people as their lives begin to intertwine while they fall in – and out – of love. Affections languish and develop as Christmas draws near.

Similar in 85%

About Time (2013)

Plot Summary:

The night after another unsatisfactory New Year party, Tim's father tells his son that the men in his family have always had the ability to travel through time. Tim can't change history, but he can change what happens and has happened in his own life – so he decides to make his world a better place... by getting a girlfriend. Sadly, that turns out not to be as easy as he thinks.

Similar in 88%

Just Friends (2005)

Plot Summary:

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.

Similar in 87%

Something Borrowed (2011)

Plot Summary:

Though Rachel (Ginnifer Goodwin) is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy (Kate Hudson). Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan (John Krasinski), Rachel's confidant, harbors a potentially explosive secret of his own.

Similar in 84%

The Proposal (2009)

Plot Summary:

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.

Similar in 90%

The Holiday (2006)

Plot Summary:

Two women, one (Cameron Diaz) from America and one (Kate Winslet) from Britain, swap homes at Christmastime after bad breakups with their boyfriends. Each woman finds romance with a local man (Jude Law, Jack Black) but realizes that the imminent return home may end the relationship.

Similar in 89%

How to Lose a Guy in 10 Days (2003)

Plot Summary:

An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana (Bebe Neuwirth), loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry (Matthew McConaughey), who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.

Similar in 83%

The Family Man (2000)

Plot Summary:

Jack's lavish, fast-paced lifestyle changes one Christmas night when he stumbles into a grocery store holdup and disarms the gunman. The next morning he wakes up in bed lying next to Kate, his college sweetheart he left in order to pursue his career, and to the horrifying discovery that his former life no longer exists. As he stumbles through this alternate suburban universe, Jack finds himself at a crossroad where he must choose between his high-power career and the woman he loves.

Similar in 83%

Love, Rosie (2014)

Plot Summary:

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? Based on Cecelia Ahern's bestselling novel, LOVE, ROSIE is a heart-warming, modern comedy-of-errors posing the ultimate question: do we really only get one shot at true love?.

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Crazy, Stupid, Love. (2011)

Plot Summary:

Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.