20 best movies like Cherry (1999)

When Elliot, a brash 23-year-old living carefree in New York City, meets the sensible Mia and receives a damning diagnosis all in the same week, his world is turned completely upside down. But as their love blossoms amidst the chaos of his treatment, they discover that Elliot's illness is not the real test of their relationship – it's everything else.

The fiancé of an African-American woman who's met with skepticism and suspicion from her father when she takes him home for the all-important introduction. As the wedding approaches, Dad must come to terms with his future son-in-law.

Having thought that monogamy was never possible, a commitment-phobic career woman may have to face her fears when she meets a good guy.

Reunited after 15 years, famous chef Sasha and hometown musician Marcus feel the old sparks of attraction but struggle to adapt to each other's worlds.

Aspiring New York City artist, John Hollar returns to his Middle America hometown on the eve of his mother’s brain surgery. Joined by his girlfriend, eight months pregnant with their first child, John is forced to navigate the crazy world he left behind.

A woman on the brink of a marriage proposal is told by a friend that she should date other men before spending the rest of her life with her boyfriend.

When a professional couple, who have lived and worked together for many years, finally decide to marry, their sudden betrothal causes many unexpected difficulties. They soon find that being married is often quite different from being "best friends."

The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.

A young woman is forced to reflect on her first relationship when she inadvertently moves into her ex boyfriend's apartment building.

Senior year of high school takes center stage as Lara Jean returns from a family trip to Korea and considers her college plans — with and without Peter.

Narcissistic, brash, and self-destructive Jimmy thinks all relationships are doomed. Cynical, people-pleasing, and stubborn Gretchen knows that relationships aren't for her. So when they meet at a wedding, it's only natural that the two of them go home together and, despite their better judgment, begin to find themselves falling for each other.

Inspired by a true story, a comedy centered on a 27-year-old guy who learns of his cancer diagnosis, and his subsequent struggle to beat the disease.

A young woman with Asperger's tries to find her first boyfriend with a little help from her older sister.

A sex therapist goes through puberty after the successful removal of a benign tumor resting against his pituitary gland. He experiences all the changes and effects of puberty over a three-week period.

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.

An ophthalmologist's mistress threatens to reveal their affair to his wife, while a married documentary filmmaker is infatuated by another woman.

When a cosmic event turns Emma's dog and cat into two perfect guys, Emma reconsiders her outlook on dating, hilariously works out her trust issues, and ultimately learns to love herself.

Xavier is a 40-year-old father of two who still finds life very complicated. When the mother of his children moves to New York, he can't bear them growing up far away from him and so he decides to move there as well.

Leah thinks all is fine coasting along in a relationship with the ever-predictable Edward until he surprises her and enrolls her in a conflict-management class. In the class, Leah finds herself locking horns with a handsome, radio talk-show host who thrives on making waves. Through the course, Leah develops new friendships, an inner strength she never knew she had and discovers real love should never mean settling for the easy and predictable.

Sidney is a writer who's just left her L.A. Times music review gig to edit New York hip-hop magazine XXL. Dre is an executive with a hip-hop record company based in New York. They've known each other since they met as children, when both discovered hip-hop for the first time. Now that they're back together, they should be perfect for each other, except that Dre's about to marry lawyer Reese and Sidney claims not to be interested in Dre romantically. Meanwhile, Dre is growing increasingly restless with his company's focus on profit over artistry, which leads to signing the gimmicky duo Ren and Ten while ignoring the talented Chris

Left broke and homeless by his wealthy parents' divorce, a young man moves in with an old friend and finally meets the woman of his dreams -- only to discover she's already dating his friend.

After her mother's death, mediocre chef Amanda Shelton is having trouble attracting customers to her family's restaurant. While shopping for ingredients, she is given a magical crab by mysterious Gene O'Reilly. Afterward, Amanda's dishes suddenly become excellent, inducing strong emotional reactions in everyone who eats them. Tom Bartlett, who is preparing to open his own eatery, tries her cooking and falls in love.

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.

After a man finally gets over his former girlfriend, who has moved to Los Angeles and become a television star, and falls in love with another woman, the former girlfriend's show is canceled and she wants him back.

Veterinarian Dr. Carly Monroe makes it a habit to stop by the local dog shelter as often as possible because she loves dogs and secretly loves the shelter’s owner, Dan. Unfortunately, he has agreed to marry his glamorous TV personality girlfriend and move to the Big Apple. With Dan’s big move looming, his sister decides to take matters into her own hands.

At breakfast, Jane announces that she and Ralph are getting married the next week. All Jane and Ralph want is a small wedding with the immediate family and no reception. This is because Jane's parents are poor and Jane and Ralph can borrow a car for their honeymoon. However, at dinner that night all Ralph's parents talk about are the big weddings they gave their daughters and everything escalates. All of a sudden, it is a big wedding breakfast with hundreds of guests. The problem is that for 12 years, Tom has been saving money to buy his own cab and license, but now that he can, all of his money is going towards a wedding neither he, or Jane or Ralph really want.

Oscar and Peter land a career-making opportunity when a Chicago tycoon chooses them to compete for the design of a cultural center. The tycoon mistakenly believes that Oscar is gay and has him spy on his mistress Amy. Oscar goes along with it and ends up falling in love with Amy.

The Malacicis, a hard-working Italian family recently immigrated from Florence, open a fancy restaurant in the Bronx, N.Y., drawing the ire of another clan. Mike and Sadie Capomezzo, equally hard-working Sicilian caterers from the area, find they cannot stand Piero and Maria Malacici. But things get complicated when the Malacicis' daughter, Gina, and the Capomezzos' son, Rosario, fall in love.

Bored with Bollywood movies but fascinated with their Hollywood counterparts from his youth, Ram dreams to become a singer and actor in America, the country where dreams are made. He is encouraged when his American-based close friend, Vijay Rao, comes for visit, and brags about driving a Mercedes and living in a penthouse.

The film tells the story of quick-witted teen Mark, contentedly living the same day in an endless loop whose world is turned upside-down when he meets mysterious Margaret also stuck in the time loop. Mark and Margaret form a magnetic partnership, setting out to find all the tiny things that make that one day perfect. What follows is a love story with a fantastical twist, as the two struggle to figure out how -- and whether -- to escape their never-ending day.

Sam and Gray are such a well-matched pair that it is difficult to believe they are brother and sister rather than husband and wife. They both share a love of 1940s movies and dancing, and when they meet Charlie, they have something else in common: They both fall in love with her. Sam must deal with unexpected feelings of jealousy, while Gray struggles to come to terms with her sexual orientation.

It's an hour before Lucy's wedding and her best friend wants to hear all about what led up to that moment. So, Lucy tells about the five men she had blind dates with over the past year (Doug, Gabriel, Bobby, Barry, and Luke) and her experiences with each one. But which one of the five men is Lucy about to walk down the aisle with?

For a long time, Natalie, an Australian architect living in New York City, had always believed that what she had seen in rom-coms is all fantasy. But after thwarting a mugger at a subway station only to be knocked out while fleeing, Natalie wakes up and discovers that her life has suddenly become her worst nightmare—a romantic comedy—and she is the leading lady.

Pledging to keep herself from being the oldest and the only woman in her entire family never to wed, Montana embarks on a thirty-day, thirty-thousand-mile expedition to charm a potential suitor into becoming her fiancé.

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?

Following both the death of her father-in-law and a divorce, Jesse, a New Yorker, returns to a small town to live with her now widowed mother-in-law. Jesse struggles to fit in with the local townsfolk who don’t welcome her with open arms to say the least. Jesse becomes acquainted with the local pastor, her widowed brother-in-law, falling in love with him, much to the dismay of the community. Things get even more complicated when her ex-husband comes calling, suspiciously trying to win her back. Between her love life and entangled in-laws, Jesse is tested as she seeks the answer to where she truly belongs.

Lucky is tricked into missing his own wedding again and has to make $25,000 so her father allows him to marry Margaret. He and business partner Pop go to New York where they run into dancing instructor Penny. She and Lucky form a successful dance partnership, but romance is blighted by his old attachment to Margaret and hers for Ricky Romero.

The weeks leading up to a young couple's wedding is comic and stressful, especially as their respective fathers try to lay to rest their feud.

It's Hollywood, 1958. Small town beauty queen and devout Baptist virgin Marla Mabrey, under contract to the infamous Howard Hughes, arrives in Los Angeles. At the airport, she meets her driver Frank Forbes, who is engaged to be married to his seventh grade sweetheart and is a deeply religious Methodist. Their instant attraction not only puts their religious convictions to the test, but also defies Hughes' number one rule: No employee is allowed to have any relationship whatsoever with a contract actress. Hughes' behavior intersects with Marla and Frank in very separate and unexpected ways, and as they are drawn deeper into his bizarre world, their values are challenged and their lives are changed.

Providing the romantic comedy genre with a decidedly queer twist, THE ONE is an effortlessly charming tale which proves that love is never simple! Hunky Daniel couldn’t have it better: great parents, a successful career and his beautiful fiancée Jen. But in his seemingly perfect life, there is one temptation- he has a thing for his adorable, openly gay former college classmate Tommy. After a few drinks, Daniel succumbs to his repressed desires sending these two on a torrid affair. Funny how love and lust have a way of messing up even the best laid plans of man!

The continuing adventures of the Portokalos family. A follow-up to the 2002 comedy, "My Big Fat Greek Wedding."

As her marriage dissolves, a Manhattan writer takes driving lessons from a Sikh instructor with marriage troubles of his own. In each other's company they find the courage to get back on the road and the strength to take the wheel.

Altruistic Jane finds herself facing her worst nightmare as her younger sister announces her engagement to the man Jane secretly adores.

A woman struggles to escape the clutches of her overbearing, co-dependent mother, while gradually falling for a sexy, sophisticated attorney.

A celebrated military contractor returns to the site of his greatest career triumphs and re-connects with a long-ago love while unexpectedly falling for the hard-charging Air Force watchdog assigned to him.

Ellie Hamilton is helping plan her little sister’s wedding taking place in Acapulco. With the nuptials just a few days away—and no sign yet of the bride and groom—Ellie must work with her ex-boyfriend to make last minute decisions and stall worried family and guests.

Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.

Alex, a lovable, unassuming dog trainer is in love with a great woman - Katherine - smart, talented, from a good family. Katherine adores Alex's quirky sense of humor, honesty and capacity to listen. Having decided to pop the question, Alex is blindsided when Katherine produces a detailed list of well-thought-out "improvements" she feels will tweak Alex on their way to becoming the ideal couple. Alex instinctively rejects the suggestion that he needs to change anything. But with the threat of a new competitor, Alex decides to "do the list." Guided by a coterie of friends that include: Dave, Alex's loyal childhood buddy, best female friend Lily, her husband Michael, and their 8 year old son, Nicky, Alex's journey has him reconsider and question his beliefs, values and world.

A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.

When their plane is rerouted due to a hurricane warning, two single female best friends find themselves competing for the same guy during an extended layover in St. Louis.