Movies like When Love Digs a Hole (2018)
The best movies like When Love Digs a Hole (2018) are The Private Lives of Pippa Lee (2009), Tall Girl (2019) and I Could Never Be Your Woman (2007). If When Love Digs a Hole hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLove Don't Co$t a Thing (2003)7.7/10 from 742 votes
- Newest$POSITIONS (2026)Released 2026
- In FrenchA Tale of Love and Desire (2021)Also in French
The Private Lives of Pippa Lee (2009)
After her much older husband forces a move to a suburban retirement community, Pippa Lee engages in a period of reflection and finds herself heading toward a quiet nervous breakdown.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisTall Girl (2019)
Jodi, the tallest girl in her high school, has always felt uncomfortable in her own skin. But after years of slouching, being made fun of, and avoiding attention at all costs, Jodi finally decides to find the confidence to stand tall.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisI Could Never Be Your Woman (2007)
A mother falls for a younger man while her daughter falls in love for the first time.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisThe Best You Can (2025)
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisMy First Mister (2001)
Leelee Sobieski is brash, abrasive and vulnerable as a teenage child of divorce who hides her pain behind a mask of hard-edged gothic rebellion. Albert Brooks plays a man who is her total opposite, a precise and well-ordered menswear store owner of forty-nine who manages limited expectations and protects lonely secrets with pleasant ritual and quiet, ironic reserve. These two total opposites collide in conflict then come together in a surprising alliance, changing each other's lives forever.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLove Don't Co$t a Thing (2003)
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisLooks That Kill (2020)
A teenager lives out the hilarious and often tragic consequences of being lethally attractive, until he meets a girl with a congenital defect.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLove & Sex (2000)
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisFriends with Kids (2012)
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisSeven Minutes in Heaven (1986)
Natalie allows her classmate Jeff, who has run away from home, to stay at her place while her father is away on a business trip. Natalie soon starts dating Jeff's friend James Casey, who isn't as faithful as she thinks, while her best friend Polly falls in love with baseball player Zoo Knudsen.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisYou Will Meet a Tall Dark Stranger (2010)
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisBreaking & Exiting (2018)
Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self discovery and love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisMelody (1971)
Two youngsters declare to their parents that they want to get married. Not sometime in the future but as soon as possible.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisOnce Upon a Time in the Midlands (2002)
Though Dek leads a simple and happy life with his girlfriend Shirley and her 12-year-old daughter Marlene, his grand, televised marriage proposal puts his devotion to the test—especially as Marlene's long-absent biological father, Jimmy, looms in the background.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisOnce Around (1991)
A struggling woman finds unexpected love with a charismatic older salesman at a real estate seminar. Their passionate relationship clashes with the values of her family, particularly her father.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLaggies (2014)
Overeducated and underemployed, 28 year old Megan is in the throes of a quarterlife crisis. Squarely into adulthood with no career prospects, no particular motivation to think about her future and no one to relate to, Megan is comfortable lagging a few steps behind - while her friends check off milestones and celebrate their new grown-up status. When her high-school sweetheart proposes, Megan panics and- given an unexpected opportunity to escape for a week - hides out in the home of her new friend, 16-year old Annika and Annika's world-weary single dad Craig.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisFire with Fire (1986)
A tough, street-smart kid serving a sentence in a state youth reformatory meets a beautiful, innocent girl studying at a nearby convent. When forbidden love blossoms between them, they must fight the prison authorities, their parents and the law.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisA Tale of Love and Desire (2021)
Ahmed, 18, is French of Algerian origin. He grew up in the Parisian suburbs. On the benches of the university, he meets Farah, a young Tunisian full of energy recently arrived from Tunis. While discovering a body of sensual and erotic Arabic literature that he never knew existed, Ahmed falls deeply in love with this girl, and although literally overwhelmed by desire, he will try to resist it.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisThe Mother (2003)
A grandmother has a passionate affair with a man half her age, who is also sleeping with her daughter.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisReal Women Have Curves (2002)
In East Los Angeles, an 18-year-old struggles between her ambitions of going to college and the desires of her domineering mother for her to get married, have children, and oversee the small, rundown family-owned textile factory.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisAshby (2015)
When new kid in town Ed Wallis is given an assignment to interview an older person, he turns to his mysterious neighbor, Ashby Holt for help. That new connection leads to unexpected journeys for both of them, as Ashby – who turns out to be a retired CIA assassin – deals with a terminal prognosis, and Ed deals with adjusting to life with his newly single mom and developing relationship with a brainy classmate, Eloise.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisKatti Batti (2015)
A man falls in love with a woman because of her outlook on life. They are in a relationship for five years until a sudden turn of events causes a problem in their relationship.
Why it matches: Similar story and style · both comedy & romance
Dirty Girl (2010)
Accompanied by her closeted gay buddy, a promiscuous teenager sets out to find her long-absent father.
Why it matches: Similar story and style · both drama & comedy
Popcorn FlickMovies like thisThe Woodcutter Story (2022)
An open-pit mine is unearthed in an idyllic town in Northern Finland. A strange chain of dreadful events affect the life of Pepe, a kind and optimistic woodcutter. But no matter what happens, Pepe seems to be fine with it, as if he holds a secret of existence that is hard to grasp.
Why it matches: Similar story and style · both drama & comedy
Feliz Cumpleaños, Eric (2025)
At his birthday party, a young introvert must confront his family's conservative ideals when his boyfriend unexpectedly shows up.
Why it matches: Similar story and style · both drama & romance
Only the Brave (1994)
Alex is in love with her best friend, Vicki, her mother has dissapeared and she sets fire to things in her spare time. Vicki comes from an abusive home and wants Alex to run away with her. Alex is a bit of a nerd and a teachers pet, so takes advantage of this by trying to seduce her drippy school teacher. Alex watches as Vicki, unable to escape her terrible homelife and an psychological wreck, sets alight to herself and burns to death.
Why it matches: Similar story and style · both drama & romance
Les amours électriques (2025)
AVA is the Artificial Intelligence that manages a dating app. Everywhere she watches men and women, their eyes glued to their cell phones. She hears their voices. Among these people, Anna is looking for love. She has no secrets for AVA. But at what cost? AVA is watching you.
Why it matches: Similar story and style · both drama & romance
Ashes Under the Sea (2014)
Irene is a mature woman who is sick and goes to Dr. Cano's medical office who informs her that she just has six months to live. Dismayed, walking aimlessly meets Jorge, an older man, who is in the same situation ..
Why it matches: Similar story and style · both drama & romance
Unexpected Fart (2017)
Min-won, who is preparing for Seoul University's rolling admissions, does not pass his English listening test due to Seul-gi's fart.
Why it matches: Similar story and style · both comedy & drama
$POSITIONS (2026)
A man tries to save his family from the throes of poverty by investing their savings into speculative cryptocurrencies. His life soon becomes an anxiety-inducing nightmare as his investment strategy turns into a full-blown gambling addiction.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like When Love Digs a Hole?
The closest matches to When Love Digs a Hole are The Private Lives of Pippa Lee (2009), Tall Girl (2019) and I Could Never Be Your Woman (2007). Below are 27 more, each with the reason it matches.
What should I watch after When Love Digs a Hole?
Start with The Private Lives of Pippa Lee (2009), the closest match to When Love Digs a Hole.
What is the highest-rated movie like When Love Digs a Hole?
Love Don't Co$t a Thing (2003), rated 7.7/10 by 742 TMDB users.
What is the newest movie like When Love Digs a Hole?
$POSITIONS (2026) is the most recent release on this list.
Are there French movies like When Love Digs a Hole?
Yes: A Tale of Love and Desire (2021) and Les amours électriques (2025).
How are movies similar to When Love Digs a Hole chosen?
First come films that Trakt’s viewers watch alongside When Love Digs a Hole, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.