Movies like Picking Up & Dropping Off (2003)
The best movies like Picking Up & Dropping Off (2003) are 'Tis the Season to be Merry (2021), Mother's Day (2016) and Crazy, Stupid, Love. (2011). If Picking Up & Dropping Off hooked you with its drama and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedCaptain Fantastic (2016)7.9/10 from 7,047 votes
- NewestPlenty of Fish (2025)Released 2025
'Tis the Season to be Merry (2021)
Looking for a fresh angle to her book on relationships, Merry heads to snow-covered Vermont. She finds a new perspective and Christmas cheer with charismatic aid worker Chris.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMother's Day (2016)
Three generations come together in the week leading up to Mother's Day.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisCrazy, Stupid, Love. (2011)
Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies 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 thisWaiting to Exhale (1995)
Cheated on, mistreated and stepped on, the women are holding their breath, waiting for the elusive "good man" to break a string of less-than-stellar lovers. Friends and confidants Vannah, Bernie, Glo and Robin talk it all out, determined to find a better way to breathe.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisSleepless in Seattle (1993)
After the death of his mother, a young boy calls a radio station in an attempt to set his father up on a date. Across the country, an engaged woman becomes convinced that they belong together, despite their never having met. Will their paths collide despite the odds?
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisEnough Said (2013)
Eva is a divorced soon-to-be empty-nester wondering about her next act. Then she meets Marianne, the embodiment of her perfect self. Armed with a restored outlook on being middle-aged and single, Eva decides to take a chance on her new love interest Albert — a sweet, funny and like-minded man. But things get complicated when Eva discovers that Albert is in fact the dreaded ex–husband of Marianne...
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisWicked Minds (2003)
Holden returns home from college and is surprised to find his overpowering competitive father married to a much younger woman Lana. Holden quickly falls for the beauty and charisma of his step mother. A passionate affair begins between son and stepmother.
Why it matches: Recommended by TMDB viewers · both drama & romance
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 thisAbout a Boy (2002)
Will Freeman is a good-looking, smooth-talking bachelor whose primary goal in life is avoiding any kind of responsibility. But when he invents an imaginary son in order to meet attractive single moms, Will gets a hilarious lesson about life from a bright, but hopelessly geeky 12-year-old named Marcus. Now, as Will struggles to teach Marcus the art of being cool, Marcus teaches Will that you're never too old to grow up.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisBlended (2014)
Recently divorced mom Lauren and widowed dad Jim let their friends push them into a blind date, which goes disastrously wrong. Unsurprisingly, neither wants to see the other ever again. However, fate intervenes when both Jim and Lauren, unbeknownst to each other, purchase one-half of the same vacation package at a South African resort for families, during spring break. They and their children are forced to share the same romantic suite and participate in a slew of family activities together.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisOne Fine Day (1996)
Melanie Parker, an architect and mother of Sammy, and Jack Taylor, a newspaper columnist and father of Maggie, are both divorced. They meet one morning when overwhelmed Jack is left unexpectedly with Maggie and forgets that Melanie was to take her to school. As a result, both children miss their school field trip and are stuck with the parents. The two adults project their negative stereotypes of ex-spouses on each other, but end up needing to rely on each other to watch the children as each must save his job. Humor is added by Sammy's propensity for lodging objects in his nose and Maggie's tendency to wander.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLabor Day (2013)
Two strangers are drawn together under incredible circumstances. What starts as an unforeseen encounter over a long holiday weekend soon becomes a second chance love story.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisThe Burning Plain (2008)
A trailer is burning in the middle of a plain. The bodies of two adulterous lovers are found. Scenes from both families, before and after the dramatic events, suggest an unusual connection between them. But what is their secret?
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisChristmas Getaway (2017)
When a reservation mix-up at a mountain resort forces a newly-single travel writer to share a cabin with a handsome widower and his precocious daughter over the holidays, their lives are transformed by the magic of Christmas and the unexpected power of love.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisWhy Did I Get Married? (2007)
Eight married college friends plus one other non-friend (all of whom have achieved middle to upper class economic status) go to Colorado for their annual week-long reunion, but the mood shifts when one couple's infidelity comes to light. As secrets are revealed, each couple begins to question their own relationship.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLast Chance Harvey (2008)
In London for his daughter's wedding, a struggling jingle-writer, Harvey Shine, misses his plane to New York, and thus loses his job. While drowning his sorrows in the airport pub, Harvey meets Kate, a British government worker stuck in an endless cycle of work, phone calls from her mother, and blind dates. A connection forms between the unhappy pair, who soon find themselves falling in love.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisRemember Me (2010)
Still reeling from a heartbreaking family event and his parents' subsequent divorce, Tyler Hawkins discovers a fresh lease on life when he meets Ally Craig, a gregarious beauty who witnessed her mother's death. But as the couple draws closer, the fallout from their separate tragedies jeopardizes their love.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisAmerican Son (2019)
Time passes and tension mounts in a Florida police station as an estranged interracial couple awaits news of their missing teenage son.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisCaptain Fantastic (2016)
Deep in the forests of the Pacific Northwest, a father devoted to raising his six kids with a rigorous physical and intellectual education is forced to leave his paradise and enter the world, beginning a journey that challenges his idea of what it means to be a parent.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Absolute CinemaMovies like thisA Woman Deceived (2017)
It’s been one year since Elizabeth’s husband, Bill, died in a tragic horseback riding accident and she is starting to move on. When she runs into Travis Brown, the cowboy she met the same weekend Bill died, the two immediately hit it off. Travis is just what Elizabeth needed to come into her life and they soon get married. When new evidence surfaces implying that Bill’s death wasn’t an accident, Elizabeth must find a way to protect herself and her son from the man she married.
Why it matches: Similar story and style · both drama
Risky Business (1926)
A domineering mother sets out to break up the romance and possible marriage of her daughter, Cecily Stoughton, with Ted Pyncheon by several contrived devices and bringing in other candidates more to her liking.
Why it matches: Similar story and style · both comedy & romance
Out on the Edge (1989)
Danny is a troubled teen with a difficult home life. His parents' marriage has disintegrated, and his father's already found someone else he'd like to wed. So, Danny turns to drugs to soothe his lost soul, and when he goes too far, his mother checks him into a psychiatric unit. Can Danny finally turn his life around, and will his father help?
Why it matches: Similar story and style · both drama
The Right Way (1970)
Ali gets a job and, by dint of dedication and patience, achieves a significant promotion and ends up becoming the manager of the company, as well as winning Meltem's love. However, this is not to the liking of his cousin Cihangir and his father, who instead are totally broke and want to get their revenge on Ali.
Why it matches: Similar story and style · both drama & romance
Revolutionary Girl Utena: The Movie (1999)
In a loose retelling of the Revolutionary Girl Utena TV series, Utena Tenjou arrives at Ohtori Academy, only to be immediately swept up in a series of duels for the hand of her classmate Anthy Himemiya and the power she supposedly holds. At the same time, Utena reunites with Touga Kiryuu, a friend from her childhood who seems to know the secrets behind the duels. Utena must discover those secrets for herself, before the power that rules Ohtori claims her and her friends, new and old.
Why it matches: Similar story and style · both drama & romance
Worth the HypeMovies like thisVic the Viking: The Magic Sword (2019)
Vic dreams of going to sea as a member of the crew captained by Halvar, his father, who unfortunately thinks that the child is too weak to embark with him and his brave warriors in search of dangerous adventures; but fate will offer Vic the opportunity to prove to Halvar that he is a true Viking.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisHelicopter Mom (2015)
Maggie Cooper thinks it would be really cool if her son Lloyd were gay. So cool, in fact, that she outs him to the entire school.
Why it matches: Similar story and style · both comedy
Plenty of Fish (2025)
It’s a date! But in the age of online dating, is it still as cute and exciting? From all the available milk substitutes for your latte, to the endless movie options on Netflix, abundance of choice has become a necessity in our modern lives. But what happens when this variety spills into our love lives? This film is about Aubrey, who for better or for worse, is on the dating apps and has a date coming up. This is not her first rodeo, and it probably won’t be her last, but we’ve scored front row seats to this particular chapter of her romantic adventures. Will this date go on Cupid's resume, or will it just be another cautionary tale?
Why it matches: Similar story and style · both drama
Vincent Before Noon (2019)
A father pays his son a visit after years of conflict and turns up in the middle of his house move. The son, Vincent, reacts violently to that intrusion. Emotionally weakened, the father involuntarily reveals the true reason of his visit, which revives the tension between them. Within a few minutes, the anger, the memories and the crossed looks move the two men deeply.
Why it matches: Similar story and style · both drama
Playing with Death (2011)
The family of Eusebio, a sick old man, believes that he has begun to lose his mind and that the stories he tells, which nobody listens to, are those of a crazy person.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Picking Up & Dropping Off?
The closest matches to Picking Up & Dropping Off are 'Tis the Season to be Merry (2021), Mother's Day (2016) and Crazy, Stupid, Love. (2011). Below are 27 more, each with the reason it matches.
What should I watch after Picking Up & Dropping Off?
Start with 'Tis the Season to be Merry (2021), the closest match to Picking Up & Dropping Off.
What is the highest-rated movie like Picking Up & Dropping Off?
Captain Fantastic (2016), rated 7.9/10 by 7,047 TMDB users.
What is the newest movie like Picking Up & Dropping Off?
Plenty of Fish (2025) is the most recent release on this list.
Are there English movies like Picking Up & Dropping Off?
Yes: 'Tis the Season to be Merry (2021), Mother's Day (2016) and Crazy, Stupid, Love. (2011).
How are movies similar to Picking Up & Dropping Off chosen?
First come films that Trakt’s viewers watch alongside Picking Up & Dropping Off, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.