Movies Like Tiptoes

If you liked Tiptoes (1927), a comedy and romance movie directed by Herbert Wilcox, 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
Let's Make Love (1960)
★ 6.4/10Also comedy and romance
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
2
A Hollywood Christmas (2022)
★ 6.1/10Also comedy and romance
Jessica, a young, up-and-coming filmmaker in Hollywood has made a name for herself directing Christmas movies. But when handsome network executive Christopher shows up threatening to halt production on her latest…
3
Girl on a Bicycle (2013)
★ 5.9/10Also comedy and romance
Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day…
4
What's Love Got to Do with It? (2023)
★ 6.1/10Also romance and comedy
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
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
Good Advice (2001)
★ 5.9/10Also comedy and romance
An investment banker loses everything and must discover what's really important in life.
7
Easy Virtue (2008)
★ 6.5/10Also comedy and romance
A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
8
The Prince & Me 4: The Elephant Adventure (2010)
★ 6.1/10Also comedy and romance
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged…
9
How to Marry a Millionaire (1953)
★ 6.8/10Also comedy and romance
Three women set out to find eligible millionaires to marry, but find true love in the process.
10
Gidget (1959)
★ 6/10Also comedy and romance
Due to an accident while swimming in the sea, Francis meets the surfer Moondoggie. She's fascinated with his sport and starts to hang out with his clique. Although they make fun of her at first, they teach her to surf…
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
The Freshman (1925)
★ 7/10Also comedy and romance
An unathletic college freshman ridiculed by his peers for his mannerisms strives to become popular by making the football team.
13
Prom Pact (2023)
★ 7.2/10Also comedy and romance
It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts…
14
Watching the Detectives (2007)
★ 6.3/10Also comedy and romance
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets…
15
Champagne Problems (2025)
★ 6/10Also romance and comedy
A driven American exec heads to Paris determined to acquire a champagne brand by Christmas — and accidentally falls for the heir to the bubbly empire.
16
Silk Stockings (1957)
★ 6.8/10Also comedy and romance
After three bumbling Soviet agents fail in their mission to retrieve a straying Soviet composer from Paris, the beautiful, ultra-serious Ninotchka is sent to complete their mission and to retrieve them. She starts out…
17
Christmas with You (2022)
★ 5.9/10Also 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.
18
This Little Love of Mine (2021)
★ 6.1/10Also romance and comedy
Laura Price is a successful San Francisco lawyer on the cusp of promotion – a far cry from her childhood growing up on a tropical island with best friends Chip and Gem. When the firm’s biggest client – Chip’s…
19
I Love You Again (1940)
★ 7.2/10Also comedy and romance
Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
20
Singin' in the Rain (1952)
★ 8.1/10Also comedy and romance
In 1927 Hollywood, a silent film star falls for a chorus girl just as he and his paranoid screen partner struggle to make the difficult transition to talking pictures.