Movies Like When Eliza Met Penny

If you liked When Eliza Met Penny, a movie, 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
Duplex (2003)
★ 6.1/10
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
2
Book Club (2018)
★ 6.2/10
Four lifelong friends decide that their lives could change by becoming nasty and reading Fifty Shades of Grey in their monthly book club to get inspiration on how to handle sexual pleasure at an elderly age.
3
The Roses (2025)
★ 6.6/10
Life seems easy for picture-perfect couple Ivy and Theo: successful careers, a loving marriage, great kids. But beneath the façade of their supposed ideal life, a storm is brewing – as Theo's career nosedives while…
4
Sideways (2004)
★ 7.1/10
Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.
5
A Nice Girl Like You (2020)
★ 5.8/10
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…
6
The Last Supper (1995)
★ 6.5/10
A group of idealistic but frustrated liberals succumb to the temptation of murdering right-wing pundits for their political beliefs.
7
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…
8
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…
9
A Night at the Roxbury (1998)
★ 6.6/10
Despite being well into adulthood, brothers Doug and Steve Butabi still live at home and work in the flower shop owned by their dad. They exist only to hit on women at discos, though they're routinely unsuccessful…
10
A Simple Favor (2018)
★ 6.6/10
Stephanie, a dedicated mother and popular vlogger, befriends Emily, a mysterious upper-class woman whose son Nicky attends the same school as Miles, Stephanie's son. When Emily asks her to pick Nicky up from school and…
11
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.
12
Moonstruck (1987)
★ 6.8/10
37-year-old Italian-American widow Loretta Castorini believes she is unlucky in love, and so accepts a marriage proposal from her boyfriend Johnny, even though she doesn't love him. When she meets his estranged younger…
13
Solo Mio (2026)
★ 7.5/10
After Matt's dreams of a picturesque Italian wedding are shattered when his fiancée leaves him at the altar, he embarks on his planned honeymoon across Italy alone, immersing himself in the country's vibrant culture…
14
Eating Raoul (1982)
★ 6.4/10
A prudish married couple feel put upon by the swingers living in their apartment building. One night, by accident, they discover a way to both rid themselves of the “perverts” down the hall and simultaneously realize…
15
The Invite (2026)
★ 7.2/10
Joe and Angela's marriage is on thin ice. When they invite their enigmatic upstairs neighbors for a dinner party, the night spirals into unexpected places. Have they reignited the spark or lit the match that burns it…
16
The Kids Are All Right (2010)
★ 6.6/10
Two women, Nic and Jules, brought a son and daughter into the world through artificial insemination. When one of their children reaches age, both kids go behind their mothers' backs to meet with the donor. Life becomes…
17
Zack and Miri Make a Porno (2008)
★ 6.3/10
Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each…
18
Spa Weekend (2026)
★ 6.5/10
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
19
Return to Me (2000)
★ 6.7/10
It took a lot of persuading to get Bob, a recently widowed architect, to go on a blind date at a quirky Irish-Italian eatery. Once there, he’s instantly smitten, not with his date, but with the sharp-witted waitress…
20
Annie Hall (1977)
★ 7.7/10
New York comedian Alvy Singer falls in love with the ditsy Annie Hall.