Movies Like Rich Boy, Rich Girl

If you liked Rich Boy, Rich Girl (2018), a comedy and drama movie directed by Judy San Roman and Andrew Damon Henriques, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Hitch (2005)
★ 6.6/10Also comedy and drama
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques…
2
L.A. Without a Map (1999)
★ 5.8/10Also drama and comedy
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a…
3
Same Time, Next Year (1978)
★ 6.5/10Also comedy and drama
A man and woman meet by chance at a romantic inn over dinner and, although both are happily married to others, they find themselves in the same bed the next morning questioning how this could have happened. They agree…
4
Lovely, Still (2009)
★ 6.6/10Also drama and romance
A holiday fable that tells the story of an elderly man discovering love for the first time.
5
Love, Weddings & Other Disasters (2020)
★ 6/10Also romance and comedy
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
6
The Other Sister (1999)
★ 6.4/10Also comedy and drama
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.
7
Christmas with You (2022)
★ 5.8/10Also romance and comedy
Feeling career burnout, pop star Angelina escapes to grant a young fan's wish in small-town New York, where she not only finds the inspiration to revitalize her career but also a shot at true love.
8
That Touch of Mink (1962)
★ 6.5/10Also comedy and romance
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a…
9
The Apartment (1960)
★ 8.2/10Also comedy and drama
Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although…
10
Thoroughly Modern Millie (1967)
★ 6.9/10Also comedy and romance
Millie Dillmount, a fearless young lady fresh from Salina, Kansas, determined to experience Life, sets out to see the world in the rip-roaring Twenties. With high spirits and wearing one of those new high hemlines, she…
11
Love Is in the Air (2023)
★ 6.2/10Also romance and comedy
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
12
Madame (2017)
★ 5.9/10Also romance and comedy
Anne and Bob, a well-to-do American couple, have just moved to a beautiful manor house in romantic Paris. To impress their sophisticated friends, they decide to host a lavish dinner party, but must disguise their maid…
13
You Will Meet a Tall Dark Stranger (2010)
★ 5.9/10Also comedy and drama
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling…
14
The Secret: Dare to Dream (2020)
★ 7.4/10Also drama and romance
A widow with three children hires a handyman to fix her house during a major storm. When not doing home repairs, he shares his philosophy of believing in the power of the universe to deliver what we want.
15
Stranded in Paradise (2014)
★ 6/10Also drama and romance
When a driven HR exec loses her high-powered job, she travels to Puerto Rico in an attempt to save her career at a business conference. But as the trip quickly becomes a disaster and a hurricane shuts down the whole…
16
The Lost Husband (2020)
★ 6.7/10Also drama and romance
Trying to put her life back together after the death of her husband, Libby and her children move to her estranged Aunt's goat farm in central Texas.
17
Good Advice (2001)
★ 5.9/10Also comedy and romance
An investment banker loses everything and must discover what's really important in life.
18
Love Sarah (2020)
★ 6.2/10Also comedy and drama
A young woman wishes to fulfill her mother's dream of opening her own bakery in Notting Hill, London. To do this, she enlists the help of an old friend and her grandma.
19
Green Card (1990)
★ 6.1/10Also comedy and romance
Urban horticulturalist Brontë Mitchell has her eye on a gorgeous apartment, but the building's board will rent it only to a married couple. Georges Fauré, a waiter from France whose visa is expiring, needs to marry an…
20
What a Way to Go! (1964)
★ 7.1/10Also comedy and romance
A four-time widow discusses her four marriages, in which all of her husbands became incredibly rich and died prematurely because of their drive to be rich.