Movies Like To Love & To Lose

If you liked To Love & To Lose, a movie directed by Ruben Zaccaroni, 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
Synecdoche, New York (2008)
★ 7.5/10
A theater director struggles with his work, and the women in his life, as he attempts to create a life-size replica of New York inside a warehouse as part of his new play.
2
Isn't It Romantic (2019)
★ 6.2/10
For a long time, Natalie, an Australian architect living in New York City, had always believed that what she had seen in rom-coms is all fantasy. But after thwarting a mugger at a subway station only to be knocked out…
3
Otherhood (2019)
★ 6.1/10
Feeling forgotten on Mother's Day, three best friends leave the suburbs and drive to New York City to surprise their adult sons.
4
The Terminal (2004)
★ 7.4/10
An Eastern European tourist unexpectedly finds himself stranded in JFK airport, and must take up temporary residence there.
5
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.
6
How to Be Single (2016)
★ 6.3/10
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions…
7
That Touch of Mink (1962)
★ 6.5/10
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a…
8
Annie Hall (1977)
★ 7.7/10
New York comedian Alvy Singer falls in love with the ditsy Annie Hall.
9
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…
10
Caught Stealing (2025)
★ 6.8/10
Burned-out ex-baseball player Hank Thompson unexpectedly finds himself embroiled in a dangerous struggle for survival amidst the criminal underbelly of late 1990s New York City, forced to navigate a treacherous…
11
Saturday Night (2024)
★ 6.7/10
At 11:30pm on October 11, 1975, a ferocious troupe of young comedians and writers changed television forever. This is the story of what happened behind the scenes in the 90 minutes leading up to the first broadcast of…
12
The Immigrant (1917)
★ 7.3/10
A European immigrant endures a challenging voyage only to get into trouble as soon as he arrives in New York.
13
Not Okay (2022)
★ 6.2/10
An ambitious young woman, desperate for followers and fame, fakes a trip to Paris to up her social media presence. When a terrifying incident takes place in the real world and becomes part of her imaginary trip, her…
14
Hard to Die (1990)
★ 6/10
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
15
The Mouse That Roared (1959)
★ 6.4/10
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
16
A Different Man (2024)
★ 6.9/10
Aspiring actor Edward undergoes a radical medical procedure to drastically transform his appearance. But his new dream face quickly turns into a nightmare.
17
Whatever Works (2009)
★ 7.1/10
Whatever Works explores the relationship between a crotchety misanthrope, Boris and a naïve, impressionable young runaway from the south, Melody. When Melody's uptight parents arrive in New York to rescue her, they are…
18
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
19
Can You Keep a Secret? (2019)
★ 6.3/10
Emma Corrigan, a girl with a few secrets, thinks she’s about to die on a turbulent plane ride. She spills them all to the handsome stranger sitting next to her. At least, she thought he was a stranger. But then, her…
20
The Sun Is Also a Star (2019)
★ 6.9/10
Two young New Yorkers begin to fall in love over the course of a single day, as a series of potentially life-altering meetings loom over their heads - hers concerning her family’s deportation to Jamaica, and his…