Movies Like Dating in Your 20s

If you liked Dating in Your 20s (2025), a comedy and music movie directed by Lily Rutterford and Lucy Minderides, 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
Footlight Parade (1933)
★ 6.8/10Also comedy and music
A fledgling producer finds himself at odds with his workers, financiers and his greedy ex-wife when he tries to produce live musicals for movie-going audiences.
2
A Day at the Races (1937)
★ 7.1/10Also comedy and music
Doctor Hugo Hackenbush, Tony, and Stuffy try and save Judy's sanitarium by winning a big race with a finicky horse owned by Judy's boyfriend Gil. There are a few problems. Hackenbush, who was recently put in charge of…
3
Love Happy (1949)
★ 5.8/10Also comedy and music
The Marx Brothers help young Broadway hopefuls when they get mixed up with gangsters due to a tin of sardines containing Romanoff diamonds.
4
A Very Jonas Christmas Movie (2025)
★ 6.2/10Also comedy and music
Kevin, Nick, and Joe Jonas face a series of escalating obstacles as they struggle to make it from London to New York in time to spend Christmas with their families.
5
Arlo the Alligator Boy (2021)
★ 6.8/10Also comedy and music
Upon learning that he is from New York City, a wide-eyed boy, who is half human and half alligator, decides to leave his sheltered life in the swamp and search for his long lost father. A musical adventure.
6
Bo Burnham: Make Happy (2016)
★ 8/10Also comedy and music
Combining his trademark wit and self-deprecating humor with original music, Bo Burnham offers up his unique twist on life in this stand-up special about life, death, sexuality, hypocrisy, mental illness and Pringles…
7
A Mighty Wind (2003)
★ 6.8/10Also comedy and music
Three eclectic, never-quite-famous folk bands come together for the first time in decades following the death of their manager to put on an reunion concert in his honor, at the request of his son.
8
Babes in Arms (1939)
★ 6.4/10Also comedy and music
Mickey Moran, son of two vaudeville veterans, decides to put up his own vaudeville show with his girlfriend Patsy Barton. But child actress Rosalie wants to make a comeback and replace Patsy both professionally and as…
9
A Song Is Born (1948)
★ 6.5/10Also comedy and music
The story of seven scholars in search of an expert to teach them about swing music. They seem to have found the perfect candidate in winsome nightclub singer Honey Swanson. But Honey's gangster boyfriend doesn't want…
10
Popstar: Never Stop Never Stopping (2016)
★ 6.6/10Also comedy and music
When his new album fails to sell records, pop/rap superstar Conner4real goes into a major tailspin and watches his celebrity high life begin to collapse. He'll try anything to bounce back, anything except reuniting…
11
The Big Store (1941)
★ 6.3/10Also comedy and music
A detective is hired to protect the life of a singer, who has recently inherited a department store, from the store's crooked manager.
12
Back to the Beach (1987)
★ 5.9/10Also comedy and music
A former beach boy and his wife go to California to visit their daughter and become part of the new beach scene.
13
Grease Live (2016)
★ 7.1/10Also music
After enjoying a holiday romance, high school students Danny and Sandy are unexpectedly reunited when she transfers to Rydell High, where she must contend with cynical Rizzo and the Pink Ladies.
14
Sing: Thriller (2024)
★ 7.1/10Also comedy and music
Buster Moon dreams up a star-studded spectacle set to Michael Jackson's "Thriller" in this animated short featuring characters from the hit "Sing" films.
15
Stuck in the Suburbs (2004)
★ 6/10Also comedy and music
Brittany Aarons is one of the many girls who has a crush on popular singer and boy-toy Jordan Cahill. However, she is bored of living a suburban existence and seeks a little something more.
16
Meet the Feebles (1989)
★ 6.3/10Also comedy and music
Heidi the Hippo, star of 'The Feebles Variety Hour', discovers her lover Bletch the Walrus is cheating on her. And with all the world waiting for the big show, the assorted co-stars must contend with drug addiction…
17
UglyDolls (2019)
★ 6.6/10Also music and comedy
In the adorably different town of Uglyville, weirdness is celebrated, strangeness is special and beauty is embraced as more than meets the eye. After traveling to the other side of a mountain, Moxy and her UglyDoll…
18
Josie and the Pussycats (2001)
★ 6.7/10Also comedy and music
Josie, Melody and Val are three small-town girl musicians determined to take their rock band out of their garage and straight to the top, while remaining true to their look, style and sound. They get a record deal…
19
Sing (2016)
★ 7.1/10Also comedy and music
A koala named Buster recruits his best friend to help him drum up business for his theater by hosting a singing competition.
20
Wayne's World (1992)
★ 6.7/10Also comedy and music
The adventures of two amiably aimless metal-head friends, Wayne and Garth. From Wayne's basement, the pair broadcast a talk-show called "Wayne's World" on local public access television. The show comes to the attention…