Movies like Dexter Jackson's Guide to Dating: The Movie
The best movies like Dexter Jackson's Guide to Dating: The Movie are What's Your Number? (2011), My Sassy Girl (2008) and Crossing Delancey (1988). If Dexter Jackson's Guide to Dating: The Movie hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedSuccubus (2024)8.3/10 from 280 votes
- NewestThe Wrong Paris (2025)Released 2025
What's Your Number? (2011)
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 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.
Why it matches: Recommended by TMDB viewers
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
Popcorn FlickMovies like thisCrossing Delancey (1988)
Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is courted by a married, worldly author, Anton, yet can't seem to shake the down-to-earth appeal of Sam, a pickle vendor.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisMy Fake Boyfriend (2022)
A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. But everything backfires when he meets the real love of his life, and breaking up with his fake boyfriend proves hard to do.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisPhffft (1954)
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 bringing them together.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisOne Day (2011)
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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisPetulia (1968)
Dr. Archie Bollen is having a midlife crisis. He's just divorced his wife and is establishing a new life for himself. One night, he catches the eye of Petulia Danner, a charming, free-spirited young woman. Petulia's vibrant personality hides her fear of her abusive husband, David, whose father is a powerful society figure. As Petulia and Archie's feelings for each other grow, they must decide what it is they truly want.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies 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
Popcorn FlickMovies like thisHow to Be Single (2016)
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisAnything for Love (2016)
Katherine, a high-powered executive who believes men are intimidated by her career, is persuaded by her friend to create an internet dating profile claiming she is an executive assistant.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisKissing Jessica Stein (2002)
Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.
Why it matches: Recommended by TMDB viewers
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
Popcorn FlickMovies like thisThe Wrong Paris (2025)
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisChasing Papi (2003)
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
Why it matches: Recommended by TMDB viewers
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
Popcorn FlickMovies like thisNever Kiss a Man in a Christmas Sweater (2020)
Single mom Maggie is facing Christmas alone until Lucas crashes into her life and becomes an unexpected house guest. Together they overcome Christmas while finding comfort in their growing bond.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSuccubus (2024)
A new father going through a marital separation joins a dating app and matches with a beautiful but mysterious young woman... whose powers of seduction and manipulation entangle him in a mystery more horrifying than he could have ever imagined.
Why it matches: Recommended by TMDB viewers
Absolute CinemaMovies like thisSidewalks of New York (2001)
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisHitch (2005)
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisYou've Got Mail (1998)
Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet—both blissfully unaware that he's trying to put her out of business.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Dexter Jackson's Guide to Dating: The Movie?
The closest matches to Dexter Jackson's Guide to Dating: The Movie are What's Your Number? (2011), My Sassy Girl (2008) and Crossing Delancey (1988). Below are 17 more, each with the reason it matches.
What should I watch after Dexter Jackson's Guide to Dating: The Movie?
Start with What's Your Number? (2011), the closest match to Dexter Jackson's Guide to Dating: The Movie.
What is the highest-rated movie like Dexter Jackson's Guide to Dating: The Movie?
Succubus (2024), rated 8.3/10 by 280 TMDB users.
What is the newest movie like Dexter Jackson's Guide to Dating: The Movie?
The Wrong Paris (2025) is the most recent release on this list.
Are there English movies like Dexter Jackson's Guide to Dating: The Movie?
Yes: What's Your Number? (2011), My Sassy Girl (2008) and Crossing Delancey (1988).
How are movies similar to Dexter Jackson's Guide to Dating: The Movie chosen?
First come films that Trakt’s viewers watch alongside Dexter Jackson's Guide to Dating: The Movie, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.