Movies like Outside Sales (2006)
The best movies like Outside Sales (2006) are I Love You Again (1940), Dean (2016) and Love, Weddings & Other Disasters (2020). If Outside Sales 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 rated¿Quieres ser mi hijo? (2023)8.4/10 from 378 votes
- NewestYoh! Bestie (2026)Released 2026
I Love You Again (1940)
Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisDean (2016)
A comedy about loss, grief, and the redemptive power of love. Dean is a NY illustrator who falls hard for an LA woman while trying to prevent his father from selling the family home in the wake of his mother's death.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisLove, Weddings & Other Disasters (2020)
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove Is in the Air (2023)
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLet's Make Love (1960)
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisYoh! Bestie (2026)
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Right Kind of Wrong (2013)
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisBye Bye Love (1995)
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, Emma. Dave, meanwhile, has an enviable problem -- he has more dates than he can handle. As they confront their post-marital challenges, the men take solace in one another's plights.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like this¿Quieres ser mi hijo? (2023)
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Absolute CinemaMovies like thisRelationship Goals (2026)
When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her priorities.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLittle Italy (2018)
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDesperados (2020)
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSex Appeal (2022)
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Incredible Jessica James (2017)
Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisHow I Got Into College (1989)
High school senior Marlon Bowne is smitten with overachieving classmate Jessica Kailo. But, if he wants to have a shot with her, he'll have to find a way to get into Ramsey College, Jessica's top choice of schools. It won't be easy, since the college is highly selective and Marlon's grades are hardly impressive. That means the lovelorn teen will have to find a way to score high on the SATs and win over the college admissions committee.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisWhat's Love Got to Do with It? (2023)
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisMy Sassy Girl (2008)
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Nice Girl Like You (2020)
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 of self-discovery, friendship, and new love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisA Hollywood Christmas (2022)
Jessica, a young, up-and-coming filmmaker in Hollywood has made a name for herself directing Christmas movies. But when handsome network executive Christopher shows up threatening to halt production on her latest movie, Jessica’s assistant, Reena, points out the irony: Jessica isn’t just trying to save her Christmas movie, she’s actually living in one. Jessica must now juggle all the classic tropes—her actors falling in and out of love, a wayward elf dog, and her own stirring romantic feelings for her perceived nemesis—in order to get her movie and her life to their happy endings.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisEasy Virtue (2008)
A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLovers and Other Strangers (1970)
Mike Vecchio and Susan Henderson are preparing for their upcoming wedding. However, they seem to be the only two people at the wedding that are happy. Mike's brother Richie and his wife Joan are going through a divorce, which is upsetting his overly devout Catholic mother Beatrice. Also, Susan's father is carrying on an affair and her sex starved older sister Wilma is going through her troubles with her husband Johnny. All this is going on while Mike's best friend Jerry is trying to bed the maid of honor, Susan's cousin Brenda.
Why it matches: Similar story and style · both comedy & romance
Waterproof (2020)
Jack is in a rut and unsure what to do with his life. He tries to stay focused and get his life in order, but all manner of distractions get in the way.
Why it matches: Similar story and style · both comedy & romance
Children of Invention (2010)
Two young children living illegally in a model apartment outside Boston are left to fend for themselves when their hardworking mother disappears
Why it matches: Similar story and style · both comedy & romance
The Captain's Paradise (1953)
Mediterranean ferryboat captain Henry St James has things well organized - a loving and very English wife Maud in Gibraltar, and the loving if rather more hot-blooded Mistress, Nita in Tangiers. A perfect life. As long as neither woman decides to follow him to the other port.
Why it matches: Similar story and style · both romance & comedy
Colonel Effingham's Raid (1946)
The story takes place in 1940. On the eve of America's entry in World War II, a colonel retired to his small Southern town, and discovers that there is a plan afoot to tear down Confederate Monument Square. He begins a campaign to rally the townspeople to save the square.
Why it matches: Similar story and style · both comedy & romance
Lulu on the Bridge (1998)
A famous jazz saxophonist's life is forever changed after he is accidentally shot. After discovering a mysterious package, he meets and falls in love with a beautiful aspiring actress, but their happiness is cut short by a series of strange, dreamlike events.
Why it matches: Similar story and style · both romance
SnoozefestMovies like thisGirls Gone Psycho (2006)
Life's always been easy for trust-fund baby Sasha Childers (Kinsey Packard), who spends her nights with her glitterati friends at the hottest clubs in town. When a sex tape surfaces that puts Sasha in the tabloids, she takes revenge on the club owner who leaked it. But her crime puts her on someone else's hit list, sending Sasha and her friends someplace they've never been: on the run. Deanna Dozier, Monterey Salka and Robert Berson co-star.
Why it matches: Similar story and style · both comedy
The Wrong Arm of the Law (1963)
The crooks in London know how it works. No one carries guns and no one resists the police. Then a new gang appears that go one better. They dress as police and steal from the crooks. This upsets the natural order of the police/criminal relationship and the police and the crooks join forces to catch the IPOs (Impersonating Police Officers), including an armoured car robbery in which the police must help the gangs to set a trap.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisSay Goodnight (2008)
Three guys tell a friend the stories of how they met the loves of their lives, and how they managed to completely screw up the relationships.
Why it matches: Similar story and style · both comedy
Symbol (2009)
A Japanese man in polka-dot pajamas wakes up in a room with no doors. Meanwhile, a middle-aged Mexican wrestler prepares for his most challenging match ever.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Outside Sales?
The closest matches to Outside Sales are I Love You Again (1940), Dean (2016) and Love, Weddings & Other Disasters (2020). Below are 27 more, each with the reason it matches.
What should I watch after Outside Sales?
Start with I Love You Again (1940), the closest match to Outside Sales.
What is the highest-rated movie like Outside Sales?
¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.
What is the newest movie like Outside Sales?
Yoh! Bestie (2026) is the most recent release on this list.
Are there English movies like Outside Sales?
Yes: I Love You Again (1940), Dean (2016) and Love, Weddings & Other Disasters (2020).
How are movies similar to Outside Sales chosen?
First come films that Trakt’s viewers watch alongside Outside Sales, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.