20 best movies like A Rainy Day in New York (2019)

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

Jenny Farrell is getting married. But how will her straight-laced family react when they find out that the woman they thought was their daughter’s roommate is actually her fiancée? As the old-fashioned Farrells attempt to come to terms with the prospect of a surprise daughter-in-law, they face a difficult choice: either adapt with the times or risk being left behind.

An adaptation of F. Scott Fitzgerald's Long Island-set novel, where Midwesterner Nick Carraway is lured into the lavish world of his neighbor, Jay Gatsby. Soon enough, however, Carraway will see through the cracks of Gatsby's nouveau riche existence, where obsession, madness, and tragedy await.

Four high school students look to redefine themselves after graduation.

Beatriz, an immigrant from a poor town in Mexico, has drawn on her innate kindness to build a career as a health practitioner. Doug Strutt is a cutthroat, self-satisfied billionaire. When these two opposites meet at a dinner party, their worlds collide, and neither will ever be the same.

A recent college graduate sets out to win back the girl of his dreams.

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

Before being judges, attorneys, or jury members, they are first of all men and women at a crossroads in their lives, with their dreams and their secrets, their hopes and their limitations, all beneath the same sun, each with their own dark side. In a lovely provincial town, during a jazz festival, life will juggle with their destinies.

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.

A small business owner is about to lose her shop to a major corporate development.

A woman at rock bottom must find her way across Los Angeles in order to crash her ex-boyfriend's engagement party.

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.

With a new iPhone, an apartment near the Grove, and a comfortable bank account left to her by her beloved late husband, Marnie Minervini has happily relocated from New Jersey to Los Angeles to be near her daughter Lori, a successful (but still single) screenwriter, and smother her with motherly love. But when the dozens of texts, unexpected visits, and conversations dominated by unsolicited advice force Lori to draw strict personal boundaries, Marnie finds ways to channel her eternal optimism and forceful generosity to change the lives of others - as well as her own - and find a new purpose in life.

A woman at a crossroads traveling to Cannes along with her successful film producer husband, finds herself on a two-day road trip with his business associate. What follows is a carefree journey replete with diversions involving picturesque sites, fine food and wine, humor, wisdom and romance - reawakening Anne's senses and a new lust for life.

Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The three young men make a pact to have fun and avoid commitment. However, when all three find themselves involved in serious relationships, they must keep their romances secret from one another.

Following a wild night out with his Best Man, Rob Anderson wakes up to find himself naked in an elevator on the morning of his wedding day and is forced to relive the morning over and over again.

A 16-year-old girl and her extended family are left reeling after her calculating grandmother unveils an array of secrets on her deathbed.

An American-born Chinese economics professor accompanies her boyfriend to Singapore for his best friend's wedding, only to get thrust into the lives of Asia's rich and famous.

Three very different people in their twenties try to figure out love, sex, identity and friendship in Los Angeles.

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.

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."

After fast-paced New York City high-end real estate broker Fiona Rangely (Lacey Chabert) gets dumped by her boyfriend, she escapes to her family’s quaint Vermont Inn for a few days to slow down and evaluate her life. When her ex-boyfriend Nate shows up at the Inn with a brand new girlfriend, Fiona quickly devises a plan to win him back: pretend the handsome and very laid- back head chef Derek (Carlo Marks) is her new boyfriend! Much to the surprise of Derek --and to Fiona herself-- in pretending to be in love, she realizes that she’s been thrown a curveball: sometimes the best things in life are worth the wait.

Three women in their thirties head to a popular Spring Break destination and try to relive the Spring Break they never had.

Meet Joel Goodson, an industrious, college-bound 17-year-old and a responsible, trustworthy son. However, when his parents go away and leave him home alone in the wealthy Chicago suburbs with the Porsche at his disposal he quickly decides he has been good for too long and it is time to enjoy himself. After an unfortunate incident with the Porsche Joel must raise some cash, in a risky way.

Four lifelong friends have their lives forever changed after reading Fifty Shades of Grey in their monthly book club.

Four girlfriends take a trip to New Orleans for an annual festival and, along the way, rediscover their wild sides and strengthen the bonds of sisterhood.

When a corporate raider threatens a hostile takeover of a 'mom and pop' company, the patriarch of the company enlists the help of his wife's attractive daughter—who is a lawyer—to stop the takeover. However, the raider soon becomes infatuated with her, and enjoys the legal manoeuvring as he tries to win her heart.

Eloise, having been relieved of maid of honor duties after being unceremoniously dumped by the best man via text, decides to attend the wedding anyway – only to find herself seated with five fellow-unwanted guests at the dreaded Table 19.

A Seattle couple travel to New York to interview colorful former dancer Tobi for research on a dissertation about dance. But soon, common niceties and social graces erode when the questions turn personal and the true nature of the interview is called into question.

When Johnny is released from prison following a forgery charge, he quickly lands a job as a short-order cook at a New York diner. Following a brief fling with waitress Cora, Frankie develops an attraction for Cora's friend and fellow waitress Frankie. While Frankie resists Johnny's charms initially, she eventually relents when her best friend, Tim, persuades her to give Johnny a chance.

Ingrid becomes obsessed with a social network star named Taylor Sloane who seemingly has a perfect life. But when Ingrid decides to drop everything and move west to be Taylor's friend, her behaviour turns unsettling and dangerous.

Vignettes weaving together the stories of six individuals in the old West at the end of the Civil War. Following the tales of a sharp-shooting songster, a wannabe bank robber, two weary traveling performers, a lone gold prospector, a woman traveling the West to an uncertain future, and a motley crew of strangers undertaking a carriage ride.

A romantic comedy that brings together three disparate characters who are learning to face a challenging and often confusing world as they struggle together against a common demon: sex addiction.

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.

A summer heat wave and a series of sexual encounters connect a group of New Yorkers.

Jerry Webster and Carol Templeton are rival Madison Avenue advertising executives who each dislike each other’s methods. After he steals a client out from under her cute little nose, revenge prompts her to infiltrate his secret "VIP" campaign in order to persuade the mystery product’s scientist to switch to her firm.

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.

The comedy follows Jefferson, a ski-bum temp worker, whose singular joy comes from an annual excursion to the slopes with fellow slacker Curtis. But when Jefferson falls for Stephanie, an ambitious go-getter, he is forced to re-evaluate his priorities.

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.

While visiting her sister in Paris, a young woman finds romance and learns her brother-in-law is a philanderer.

Romantic comedy about two young men, their relationship and their relationship with their mothers.

Happily married for three years, Ann and David Smith live in New York. One morning Ann asks David if he had to do it over again, would he marry her? To her shock, he answers, "No". Later that day, they separately discover that, due to a legal complication, they are not legally married.

The separation of a long married couple goes awry when they fall for each other again.

Four years into his first stable relationship, a man finds out that he is pregnant with his partner's baby.

It's graduation day at Huntington Hills High, and you know what that means - time to party. And not just any party, either. This one will be a night to remember, as the nerds become studs, the jocks are humiliated, and freshman crushes blossom into grown-up romance.

Two parents fall in love over the course of a single day while playing hooky from their children's college tour.

After her fiance is falsely imprisoned, a pregnant African-American woman sets out to clear his name and prove his innocence.

Victor, a disillusioned sexagenarian, sees his life turned upside down on the day when Antoine, a brilliant entrepreneur, offers him a new kind of attraction: mixing theatrical artifices and historical reconstruction, this company offers his clients a chance to dive back into the era of their choice. Victor then chose to relive the most memorable week of his life: the one where, 40 years earlier, he met the great love.

Tony Lip, a bouncer in 1962, is hired to drive pianist Don Shirley on a tour through the Deep South in the days when African Americans, forced to find alternate accommodations and services due to segregation laws below the Mason-Dixon Line, relied on a guide called The Negro Motorist Green Book.

When he suddenly finds himself without his long-standing blue-collar job, Larry Crowne enrolls at his local college to start over. There, he becomes part of an eclectic community of students and develops a crush on his teacher.