Movies Like Damsels in Distress

If you liked Damsels in Distress (2012), a comedy and drama movie directed by Whit Stillman, 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
St. Elmo's Fire (1985)
★ 6.1/10Also drama and romance
Reluctant to let go of college life, a close-knit team of seven friends--irresponsible saxophone player Billy, young Republican Alec, his girlfriend Leslie, struggling journalist Kevin, drama queen Jules, lovesick…
2
The Big Picture (1989)
★ 5.9/10Also comedy and romance
Hollywood beckons for recent film school grad Nick Chapman, who is out to capitalize on the momentum from his national award-winning student film. Studio executive Allen Habel seduces Nick with a dream deal to make his…
3
XX/XY (2002)
★ 6/10Also drama and comedy
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
4
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…
5
The Shape of Things (2003)
★ 6.2/10Also comedy and drama
Quiet, unassuming Adam is changing in a major way, thanks to his new girlfriend, art student Evelyn. Adam's friends are a little freaked by the transformation.
6
Am I OK? (2024)
★ 6.3/10Also comedy and romance
Lucy and Jane have been best friends for most of their lives and think they know everything there is to know about each other. But when Jane announces she's moving to London, Lucy reveals a long-held secret. As Jane…
7
Ten Inch Hero (2007)
★ 7/10Also comedy and drama
Four friends search for love and happiness while working at a California sandwich shop.
8
Love Don't Co$t a Thing (2003)
★ 7.7/10Also comedy and drama
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.
9
The Sisterhood of the Traveling Pants 2 (2008)
★ 6.3/10Also comedy and drama
Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate paths for their first year of college and…
10
The Clique (2008)
★ 5.9/10Also comedy and drama
A young girl tries to fit in with a clique of popular middle school girls after moving into the guest house of one of their homes.
11
Sitting in Bars with Cake (2023)
★ 7/10Also romance and comedy
Extrovert Corinne convinces Jane, a shy, talented baker, to commit to a year of bringing cakes to bars, to help her meet people and build confidence. But when Corinne receives a life-altering diagnosis, the pair faces…
12
Carnal Knowledge (1971)
★ 6.6/10Also drama and romance
Two lifelong friends navigate complex sexual encounters and emotional entanglements, wrestling with societal norms and personal desires.
13
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.
14
Young People Fucking (2007)
★ 5.9/10Also comedy and drama
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by…
15
Why Did I Get Married Again? (2026)
★ 6.8/10Also comedy and romance
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"
16
All About Sex (2020)
★ 6/10Also comedy and drama
Three friends in their mid-20s struggle to navigate their professional and personal lives, colliding head on with the messy, hilarious and dreadful growing pangs of adulthood.
17
Someone Great (2019)
★ 6.4/10Also comedy and romance
An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one…
18
Friends with Kids (2012)
★ 5.9/10Also comedy and drama
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can…
19
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…
20
Delirious (2007)
★ 6.3/10Also comedy and drama
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved…