Movies Like Dennis & Henry's Post-Divorce Checklist

If you liked Dennis & Henry's Post-Divorce Checklist (2022), a movie directed by Bryan Wilson and Raymond Kester, 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. Vincent (2014)
★ 7.1/10
A young boy whose parents just divorced finds an unlikely friend and mentor in the misanthropic, bawdy, hedonistic, war veteran who lives next door.
2
The Rebound (2009)
★ 6.5/10
Upon discovering her husband's infidelity, Sandy leaves the suburbs and moves into the city. There, she befriends Aram, a guy whose wife only married him so she could get a green card. Sandy hires Aram to be her nanny…
3
Red, White & Royal Blue (2023)
★ 7.9/10
After an altercation between Alex, the president's son, and Britain's Prince Henry at a royal event becomes tabloid fodder, their long-running feud now threatens to drive a wedge in U.S./British relations. When the…
4
What's Your Number? (2011)
★ 6.5/10
Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96…
5
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.
6
The F**k-It List (2020)
★ 6/10
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
7
High Society (1956)
★ 6.8/10
With socialite Tracy Lord about to remarry, her ex-husband - with the help of a sympathetic reporter - has 48 hours to convince her that she really still loves him.
8
Clueless (1995)
★ 7.2/10
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her…
9
Phffft (1954)
★ 6.2/10
Robert and Nina Tracey resolve to live separate lives when their eight-year marriage dissolves into disagreements and divorce. But their separate attempts to get back out on the dating scene have a funny way of…
10
The Other Woman (2014)
★ 6.4/10
After discovering her boyfriend is married, Carly soon meets the wife he's been cheating on. And when yet another affair is discovered, all three women team up to plot mutual revenge on the three-timing SOB.
11
Bye Bye Love (1995)
★ 6.1/10
With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter…
12
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…
13
The Mighty (1998)
★ 7.2/10
Kevin, an intelligent guy helps out Maxwell to improve his reading skills. In return, Kevin wants Maxwell to take him out places since he is not authorized to go out. Being the social outcasts of the town, Kevin and…
14
One Day (2011)
★ 7.4/10
After spending the night together on the eve of their college graduation, Dexter and Emma are shown each year on the same date to see where they are in their lives. They are sometimes together, and sometimes not.
15
Creed III (2023)
★ 7.1/10
After dominating the boxing world, Adonis Creed has thrived in his career and family life. When a childhood friend and former boxing prodigy, Damian Anderson, resurfaces after serving a long sentence in prison, he is…
16
Adopt a Highway (2019)
★ 6.9/10
Russ Millings has just been released from prison after serving 21 years for a 3rd strike conviction for possessing an ounce of marijuana. As he tries to adapt to a world he doesn’t recognize – including trying to learn…
17
Racing with the Moon (1984)
★ 6.3/10
In a small coastal California town, Henry and Nicky are pals from blue collar families with only a short time before they ship off to World War II. Henry begins romancing new-to-town Caddie Winger, believing her to be…
18
Sidelined: The QB and Me (2025)
★ 6.5/10
Dallas, a burdened but headstrong dancer, is determined to get into the best dance school in the country—her late mother’s alma mater. However, that dream is suddenly derailed when the cheeky yet secretly grieving…
19
St. Elmo's Fire (1985)
★ 6.1/10
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…
20
Flipped (2010)
★ 8/10
When Juli meets Bryce in the second grade, she knows it's true love. After spending six years trying to convince Bryce the same, she's ready to give up - until he starts to reconsider.