Movies Like Charming Encounters

If you liked Charming Encounters (2026), a movie directed by Mason, 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
The Map That Leads to You (2025)
★ 6.7/10
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life…
2
The Perfect Catch (2017)
★ 6.3/10
When Jessica Parker’s former high school boyfriend, superstar baseball player Chase Taynor, returns to town, she finds the inspiration to reinvent her struggling diner… and revisits the past to find something even…
3
The Station Agent (2003)
★ 7.3/10
When his only friend dies, a man born with dwarfism moves to rural New Jersey to live a life of solitude, only to meet a chatty hot dog vendor and a woman dealing with her own personal loss.
4
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.
5
When Harry Met Sally... (1989)
★ 7.4/10
Sex always gets in the way of friendships between men and women. At least, that's what Harry Burns believes. So when Harry meets Sally Albright and a deep friendship blossoms between them, Harry's determined not to let…
6
Love of Your Life (2026)
★ 6.8/10
After a chance encounter sparks a sweeping romance, Maya's future is suddenly upended, sending her on an unexpected journey to love and live again.
7
Someone Great (2019)
★ 6.4/10
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…
8
The Adjustment Bureau (2011)
★ 6.8/10
A man glimpses the future Fate has planned for him – and chooses to fight for his own destiny. Battling the powerful Adjustment Bureau across, under and through the streets of New York, he risks his destined greatness…
9
House of D (2004)
★ 6.3/10
In the present, artist Tom Warshaw recalls his traumatic coming of age. As a 13-year-old growing up in New York City in 1973, Tom hangs out with Pappass, a mentally disabled man. With Tom's mother battling depression…
10
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
11
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…
12
Book Club: The Next Chapter (2023)
★ 6.3/10
Four best friends take their book club to Italy for the fun girls' trip they never had. When things go off the rails and secrets are revealed, their relaxing vacation turns into a once-in-a-lifetime cross-country…
13
A Big Bold Beautiful Journey (2025)
★ 6.1/10
Sarah and David are single strangers who meet at a mutual friend’s wedding and soon, through a surprising twist of fate, find themselves on a funny, fantastical, sweeping adventure together where they get to re-live…
14
Anomalisa (2015)
★ 7.1/10
An inspirational speaker becomes reinvigorated after meeting a lively woman who shakes up his mundane existence.
15
Monday (2021)
★ 6.5/10
A spark on a Friday can lead to a sizzling weekend fling, but what happens when you get to the inevitable Monday?
16
The Best of Me (2014)
★ 7.5/10
A pair of former high school sweethearts reunite after many years when they return to visit their small hometown.
17
Hello, Dolly! (1969)
★ 7/10
Dolly Levi is a strong-willed matchmaker who travels to Yonkers, New York in order to see the miserly "well-known unmarried half-a-millionaire" Horace Vandergelder. In doing so, she convinces his niece, his niece's…
18
French Girl (2024)
★ 6.2/10
Sweet Gordon, an affable English teacher in Brooklyn, has beaten the odds; a French Girl has fallen in love with him and he’s fallen even harder back. But their future is thrown into limbo when she interviews for an…
19
One Night Only (2026)
★ 6.4/10
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
20
My Dinner with Andre (1981)
★ 7.5/10
Wally, a struggling playwright and actor, reluctantly agrees to catch up with his old friend Andre, a theater director who disappeared several years prior in order to travel the world. Meeting at a posh Manhattan…