20 best movies like Kissing Jessica Stein (2001)

Sidney is a writer who's just left her L.A. Times music review gig to edit New York hip-hop magazine XXL. Dre is an executive with a hip-hop record company based in New York. They've known each other since they met as children, when both discovered hip-hop for the first time. Now that they're back together, they should be perfect for each other, except that Dre's about to marry lawyer Reese and Sidney claims not to be interested in Dre romantically. Meanwhile, Dre is growing increasingly restless with his company's focus on profit over artistry, which leads to signing the gimmicky duo Ren and Ten while ignoring the talented Chris

Sam and Gray are such a well-matched pair that it is difficult to believe they are brother and sister rather than husband and wife. They both share a love of 1940s movies and dancing, and when they meet Charlie, they have something else in common: They both fall in love with her. Sam must deal with unexpected feelings of jealousy, while Gray struggles to come to terms with her sexual orientation.

Nora Wilder (Parker Posey), a single, career woman works at a Manhattan boutique hotel where her excellent skills in guest relations lack in the romantic department. If it is not her loving and dominant mother (Gena Rowlands) attempting to set her up that consistently fail, she has her friend’s (Drea de Matteo) disastrous blind dates to rely on as a backup for further dismay. She's surrounded by friends who are all happily engaged or romantically involved and somehow, love escapes Nora -- until she meets an unusual Frenchman (Melvil Poupaud) who helps her discover life beyond her self-imposed boundaries.

An emotionally and sexually charged journey through the love, addiction, and friendship of two men. Documentary filmmaker Erik and closeted lawyer Paul meet through a casual encounter, but they find a deeper connection and become a couple. Individually and together, they are risk takers—compulsive, and fueled by drugs and sex. In an almost decade-long relationship defined by highs, lows, and dysfunctional patterns, Erik struggles to negotiate his own boundaries and dignity and to be true to himself.

Three very different people in their twenties try to figure out love, sex, identity and friendship in Los Angeles.

An aspiring actor and his girlfriend handle life's frustrations, while his friend seeks fulfillment with a blonde.

Xavier is a 40-year-old father of two who still finds life very complicated. When the mother of his children moves to New York, he can't bear them growing up far away from him and so he decides to move there as well.

A man with a "doormat" personality tries standing up for himself for a change in this comedy. Mild mannered tax accountant Elliot Sherman is what he calls a "Baxter": the kind of calm, unexciting fellow who "wears sock garters" and "enjoys raking leaves." Loved by bosses and parents, Elliot is a perfectly nice guy. And that's his problem.

After her mother's death, mediocre chef Amanda Shelton is having trouble attracting customers to her family's restaurant. While shopping for ingredients, she is given a magical crab by mysterious Gene O'Reilly. Afterward, Amanda's dishes suddenly become excellent, inducing strong emotional reactions in everyone who eats them. Tom Bartlett, who is preparing to open his own eatery, tries her cooking and falls in love.

It's New York City in 1981, and various twentysomethings are converging on a New Year's Eve party.

Jewish Jack-the-lad David seriously fancies smart, rich Anglo-Saxon Carrie as soon as he first offends her in a Boston bar. They run into each other again and though she still says she finds him appalling he works on it and they are soon together. His even more reprehensible best mate and her blousy best friend watch bemused as the two fall deeply in love and then apparently as fatally out again

Michael and Robert, two gay men living in Brooklyn, spend their last day together before Robert leaves for Africa on work assignment. Michael still has feelings for his friend Nick, who has AIDS.

Megan is an all-American girl. A cheerleader. She has a boyfriend. But Megan doesn't like kissing her boyfriend very much. And she's pretty touchy with her cheerleader friends. Her conservative parents worry that she must be a lesbian and send her off to "sexual redirection" school, where she must, with other lesbians and gays learn how to be straight.

A meditation on love and its various incarnations, set within a community of friends in Oregon. It is described as an exploration of the magical, mysterious and sometimes painful incarnations of love.

Although strangers Sara and Jonathan are both already in relationships, they realize they have genuine chemistry after a chance encounter – but part company soon after. Years later, they each yearn to reunite, despite being destined for the altar. But to give true love a chance, they have to find one another again.

A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered around two working-class New York City couples.

Three high school students experience the perks and pitfalls of love in director Leste Chen’s sensitive tale of friendship and yearning.

No sooner does Italian-American widow Loretta accept a marriage proposal from her doltish boyfriend, Johnny, than she finds herself falling for his younger brother, Ronny. She tries to resist, but Ronny lost his hand in an accident he blames on his brother, and has no scruples about aggressively pursuing her while Johnny is out of the country. As Loretta falls deeper in love, she comes to learn that she's not the only one in her family with a secret romance.

A successful gay male escort describes in a series of confessions his tangled romantic relationships with his two roommates and an older, enigmatic male client.

During shopping for Christmas, Frank and Molly run into each other. This fleeting short moment will start to change their lives, when they recognize each other months later in the train home and have a good time together. Although both are married and Frank has two little kids, they meet more and more often, their friendship becoming the most precious thing in their lives.

It's lust at first sight when Gabriel, a songwriter with Broadway ambitions, runs into Mark, a hot go-go dancer at a local gay club. They head to Gabriel's place to seal the deal, but are thwarted when Gabriel's roommate Rich arrives with opposing plans for their closet-sized apartment. It's the first of many sexual obstructions in a wild night that leaves the pair physically unsatisfied, but developing an unforeseen romantic bond nevertheless.

An aspiring dancer moves to New York City and becomes caught up in a whirlwind of flighty fair-weather friends, diminishing fortunes and career setbacks.

The wife of a pastor who preaches against homosexuality embarks on an affair with a female writer.

High school athlete Cyd Loughlin lives alone with her depressive father in South Carolina, perpetually longing to get away from it all. When her aunt, famous novelist Miranda Ruth, agrees to host her for a few weeks during the summer, Cyd jumps at the opportunity. While there, she falls for a girl in the neighborhood, even as she and her aunt gently challenge each other in the realms of sex and spirit.

A Brooklyn teenager juggles conflicting identities and risks friendship, heartbreak, and family in a desperate search for sexual expression.

Leonardo is a blind teenager dealing with an overprotective mother while trying to live a more independent life. To the disappointment of his best friend, Giovana, he plans to go on an exchange program abroad. When Gabriel, a new student in town, arrives at their classroom, new feelings blossom in Leonardo making him question his plans.

Feeling abandoned by her therapist who's gone on an extended vacation, beautiful Lindsay gets help with her fear of commitment from an ad hoc support group formed by other New Yorkers also left high and dry by their shrinks. But when her pals dare her to date fellow group member A.J., Lindsay begins to wonder if she's finally found her match.

Michel dreams of a perfect meeting with the woman of his dreams, entirely due to chance, as his parents and grandparents experienced. Vincent, Michel's contrast, is completely different. He is more the man of the direct approach and he follows his...! The two childhood friends Michel and Vincent, with completely opposite views when it comes to women, soon discover the limits of their respective techniques when they meet Angèle and Nathalie.

THE EXTRA MAN is a sophisticated and moving comedy from filmmakers Shari Springer Berman and Robert Pulcini. THE EXTRA MAN follows Louis Ives (Paul Dano), a lonely dreamer who fancies himself the hero of an F. Scott Fitzgerald novel. When a deeply embarrassing incident forces him to leave his job at an exclusive Princeton prep school, Louis heads to New York City to make a fresh start. He quickly finds a 9 to 5 job at an environmental magazine, where he encounters an entrancing, green-obsessed co-worker Mary (Katie Holmes).

Jo is chained down in a dead end supermarket job while all her friends are all out on their own separate adventures. But a chance encounter with some diamond thieves sends their separate worlds on a collision course with not only each other, but fate itself.

A socially shunned columnist finds his romantic match online, but messaging under the wrong account causes his sleazy roommate’s picture to be forwarded, creating an identity mix-up.

Sex sells in America and these guys know it. The Amateurs follows a small town band of loveable losers who hit upon an idea that can make their dreams and fantasies come true. Thinking they've found the road to riches and fame they decide to make the world's most innocent adult film. Everyman's fantasy turns into a hilarious misadventure when they find they're in way over their heads.

When Lenny and his wife, Amanda, adopt a baby, Lenny realizes that his son is a genius and becomes obsessed with finding the boy's biological mother in hopes that she will be brilliant too. But when he learns that Max's mother is Linda Ash, a kindhearted prostitute and porn star, Lenny is determined to reform her immoral lifestyle. A Greek chorus chimes in to relate the plot to Greek mythology in this quirky comedy.

A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.

Celebrated European actor Sophie Bernard is in Montreal shooting a movie, and she's taking the opportunity to visit her gay son Thomas in the hope of bridging the rift that's grown between them. But Thomas has his own agenda for their time together; he intends to finally get some answers as to the identity of his father. Meanwhile, at Ville-Marie Hospital, paramedic Pierre struggles with PTSD, and though he has support in Marie, a nurse who keeps the overflowing emergency room running, it's uncertain whether he'll remain able to cope with the high intensity of his work. Each of these four characters is dealing with emotional damage — and on one dark Montreal night, their lives will all intersect in a fateful occurrence at Ville-Marie.

Unsure of what to do next, 23-year-old Marnie tries her best to navigate life after college. Still partying like there's no tomorrow, Marnie drags herself out of bed for her miserable temp job and can't decide whether she's wasting her time going after best buddy Alex, who doesn't seem to be interested.

Smooth advertising executive David is in a relationship with yoga teacher Juliette. Then his eye is caught by Sophie, the girlfriend of his best friend Wim, a fashion photographer. Things get completely out of hand during a campaign for augmented reality-glasses, for which David designs an avatar of the coveted Sophie.

Though Rachel (Ginnifer Goodwin) is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy (Kate Hudson). Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan (John Krasinski), Rachel's confidant, harbors a potentially explosive secret of his own.

Life has its downs for James, living with his mom in Chicago at 39, an aging performer at Second City, eating and weighing too much. A woman he's been dating drops him, as does his agent, her brother. James turns down roles in local TV, roles that make him sad. Someone's remaking his favorite movie, "Marty," a role he'd love, but he doesn't even get an audition.

A rags-to-riches story of two friends, a small-time inventor and a sharky salesman, who hit rock bottom before coming up with a gizmo that becomes a worldwide phenomenon.

When Johnny is released from prison following a forgery charge, he quickly lands a job as a short-order cook at a New York diner. Following a brief fling with waitress Cora, Frankie develops an attraction for Cora's friend and fellow waitress Frankie. While Frankie resists Johnny's charms initially, she eventually relents when her best friend, Tim, persuades her to give Johnny a chance.

Maurice, a reticent young homeless man, somehow manages to get by in Brooklyn; he spends his nights in parked cars until he finds himself at Bizarre, an underground club renowned for its burlesque shows. Maurice is fascinated by the club’s playful revues celebrating self-determined sexuality and creative otherness, and the two female club owners both adore him. He soon becomes a part of their self-selected family, and begins to bond with introverted Luka. But Maurice turns his back on Luka’s growing affection. Running away from his true emotions he drifts aimlessly through the city. He tries to find his feet at a boxing club, where he meets Charlie. Unable to withstand the pressure of his repressed feelings, Maurice unleashes a mounting foment of emotions, pervaded by tenderness and menace.

ARRANGED centers on the friendship between an Orthodox Jewish woman and a Muslim woman who meet as first-year teachers at a public school in Brooklyn. Over the course of the year they learn they share much in common - not least of which is that they are both going through the process of arranged marriages.

On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to ... lovers?

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.

It's an hour before Lucy's wedding and her best friend wants to hear all about what led up to that moment. So, Lucy tells about the five men she had blind dates with over the past year (Doug, Gabriel, Bobby, Barry, and Luke) and her experiences with each one. But which one of the five men is Lucy about to walk down the aisle with?

During their travels from Chicago to New York, Harry and Sally Will debate whether or not sex ruins a perfect relationship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

Morgan is the inspiring story of Morgan Oliver, a gay young athlete determined that a bicycle accident that left him paralyzed will not change him. He takes a chance on love when he meets Dean Kagen on a basketball court. Dean helps Morgan train for the same race in which he had his accident. But when he sees that Morgan will risk everything to win, Dean walks out. Left alone to face the race and demons that caused his accident, Morgan teeters between what he needs and what he wants. Can he find the strength to pull himself back up again?

Desperate to be rid of her toddler, a dissatisfied Beverly Hills housewife hires a stranger to babysit and ends up getting much more than she bargained for.

A gay couple takes a trip to Argentina in search of a new beginning, but instead begins drifting even further apart.