Movies Like Kissing Jessica Stein
If you loved Kissing Jessica Stein's Comedy storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
The Incredible Jessica James
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.
Chasing Amy
Holden and Banky are comic book artists. Everything is going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's a lesbian.
Something New
Kenya McQueen thought she had it all: a successful career, good friends and family. There was just one thing she didn't have under control: her love life. All that changes when she meets sexy, free-spirited Brian Kelly. But when her ideal man arrives on the scene, Kenya must decide between the relationship everyone expects and the romance no one expected.
Trick
Gabriel is a young, aspiring musical composer whose life seems stuck in the First Act. When his new musical number gets a critical reception, a theatre colleague, Perry, tells Gabriel that he needs to get a life before he can write about one – so he heads straight for his local gay bar.
Author! Author!
A broadway playwright is burning the candle at both ends. He is dealing with pressure from a production nearing premiere, a wife who is leaving him, and 5 children 4 of which belong to her.
The Wrong Paris
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.
What's Your Number?
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.
Someone Like You...
Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.
More Movies Like Kissing Jessica Stein
Set It Up
Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.
The Thing About Harry
Two high school enemies, uber-jock Harry and out-and-proud Sam, are forced to share a car ride to their Missouri hometown for a friend's engagement party on Valentine's Day. Things take a turn when Sam learns Harry has come out.
(Untitled)
A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.
About Last Night
Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to navigate the relationship minefields from the bar to the bedroom and are eventually put to the test in the real world.
Someone Great
An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one outrageous last adventure in New York City.
Crossing Delancey
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.
How to Be Single
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.
Much Ado About Nothing
In this Shakespearean farce, Hero and her groom-to-be, Claudio, team up with Claudio's commanding officer, Don Pedro, the week before their wedding to hatch a matchmaking scheme. Their targets are sharp-witted duo Benedick and Beatrice -- a tough task indeed, considering their corresponding distaste for love and each other. Meanwhile, meddling Don John plots to ruin the wedding.
Shiva Baby
College student Danielle must cover her tracks when she unexpectedly runs into her sugar daddy at a shiva - with her parents, ex-girlfriend and family friends also in attendance.
School Dance
High schooler Jason has found his dream girl—the gorgeous Anastacia. There’s just one problem: she doesn’t know he exists. If he can win a spot on the school’s hottest dance crew, Jason might have a shot. But before he does, he’ll have to overcome his battle-ax of a mother, survive Anastacia’s gangsta brother, and pass the crew’s initiation—in this fresh, sexy, and outrageously funny comedy.
How I Got Into College
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 These Movies Are Similar
These recommendations share core qualities with Kissing Jessica Stein (2002): Comedy themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Kissing Jessica Stein.
See full details for Kissing Jessica Stein (2002)