Movies Like Captain Pickles

If you liked Captain Pickles (2024), a comedy and drama movie directed by Kyle Larsen, 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
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…
2
Chéri (2009)
★ 6.1/10Also drama and comedy
The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
3
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.
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
How to Please a Woman (2022)
★ 6.3/10Also romance and comedy
When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.
6
I Met a Girl (2020)
★ 6.4/10Also romance and drama
An aspiring musician struggling with schizophrenia falls for a mysterious woman who may be all in his head. When she suddenly vanishes, he takes off on a cross-country journey across Australia to find her, forcing his…
7
Enemies, a Love Story (1989)
★ 6.2/10Also comedy and drama
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
8
Voicemails for Isabelle (2026)
★ 8.3/10Also romance and comedy
A young woman's hilariously confessional voicemails to her late sister are unknowingly redirected to a stranger, who begins to fall in love from afar.
9
He Said, She Said (1991)
★ 5.9/10Also comedy and drama
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions…
10
Which Brings Me to You (2023)
★ 6.3/10Also romance and comedy
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of…
11
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…
12
Breaking & Exiting (2018)
★ 6/10Also comedy and drama
Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self…
13
Love in Taipei (2023)
★ 6.8/10Also romance and comedy
A young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance.
14
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.
15
Cyrus (2010)
★ 5.9/10Also comedy and drama
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before…
16
Rosaline (2022)
★ 7.1/10Also romance and drama
Left heartbroken after Romeo begins to pursue her cousin Juliet, Rosaline schemes to foil the famous romance and win back her guy in this comedic twist of Shakespeare's Romeo and Juliet.
17
Love & Sex (2000)
★ 6.2/10Also comedy and drama
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back…
18
A California Christmas: City Lights (2021)
★ 6.6/10Also romance and comedy
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
19
The Best You Can (2025)
★ 7/10Also comedy and romance
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside…
20
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…