Movies Like Indian Summer

If you liked Indian Summer (1991), a movie directed by Paul Thomas, 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
Set It Up (2018)
★ 6.9/10
Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.
2
Upgraded (2024)
★ 7.2/10
Ana is an ambitious intern dreaming of a career in the art world while trying to impress her demanding boss Claire. When she's upgraded to first class on a work trip, she meets handsome Will, and Ana pretends to be her…
3
White Palace (1990)
★ 6.7/10
Max Baron is a Jewish advertising executive in his 20s who's still getting over the death of his wife. Nora Baker is a 40-something diner waitress who enjoys the wilder side of life. Mismatched or not, their attraction…
4
Sweet November (2001)
★ 6.9/10
Nelson is a man devoted to his advertising career in San Francisco. One day, while taking a driving test at the DMV, he meets Sara. She is very different from the other women in his life. Nelson causes her to miss out…
5
The Shop Around the Corner (1940)
★ 8.1/10
Two employees at a gift shop can barely stand one another, without realising that they are falling in love through the post as each other's anonymous pen pal.
6
The Object of My Affection (1998)
★ 5.8/10
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
7
The Ugly Truth (2009)
★ 6.5/10
A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever…
8
Cashback (2007)
★ 7/10
After a painful breakup, Ben develops insomnia. To kill time, he starts working the late night shift at the local supermarket, where his artistic imagination runs wild.
9
Hello, My Name Is Doris (2015)
★ 6.4/10
A self-help seminar inspires a sixty-something woman to romantically pursue her younger co-worker.
10
Not Easily Broken (2009)
★ 6.3/10
A car accident and shifting affections test the bond between a married couple.
11
Phantom Thread (2017)
★ 7.3/10
In 1950s London, a renowned dressmaker's meticulous lifestyle begins drastically changing as his relationship with his young muse intensifies.
12
The Hating Game (2021)
★ 7.3/10
Resolving to achieve professional success without compromising her ethics, Lucy embarks on a ruthless game of one-upmanship against cold and efficient nemesis Joshua, a rivalry that is complicated by her growing…
13
Pretty Woman (1990)
★ 7.4/10
Vivian is a carefree, streetwise diamond in the rough when she meets sophisticated billionaire Edward in a chance encounter that turns into a week-long business arrangement. But Vivian's energetic spirit challenges…
14
Sex and Death 101 (2007)
★ 6.2/10
A guy's life is turned around by an email, which includes the names of everyone he's had sex with and ever will have sex with. His situation gets worse when he encounters a femme fatale who targets men guilty of sex…
15
Hitch (2005)
★ 6.6/10
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…
16
That Awkward Moment (2014)
★ 6.1/10
Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The…
17
(500) Days of Summer (2009)
★ 7.3/10
Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went…
18
Heatwave (2022)
★ 6.2/10
A woman's life takes an unexpected turn when she falls for her boss's wife. She must soon defend herself as she becomes entangled in a web of malice.
19
¿Quieres ser mi hijo? (2023)
★ 8.4/10
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
20
Chéri (2009)
★ 6.1/10
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.