Best movies like Kissing Jessica Stein

A wealthy woman from Manhattan's Upper East Side struggles to deal with her new identity and her sexuality after her husband of 16 years leaves her for a younger woman.

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.

At her husband's funeral, Pearl, Jewish mother of two divorced and antagonistic daughters, meets an old Italian friend of her husband, whose advice years previously had stopped the husband leaving home. For 23 years he, now a widower, has secretly loved Pearl...

Nate, a 19 year old film student, and Margaret, a 52 year old spinster, are best friends in an odd, quirky, totally working kind of way... until Nate's audacious classmate Darla sets him up on a date with James. Nate's new life shakes apart his friendship with Margaret, just as she is trying to start a career as a stand-up comedian. Written by Anonymous (IMDB.com).

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.

A semi-paralyzed radio reporter is sent out to investigate a story that leads him into an odd subculture and on a journey of disturbing self-realization.

Best friends since they were kids, Rabbi Jacob Schram and Father Brian Finn are dynamic and popular young men living and working on New York's Upper West Side. When Anna Reilly, once their childhood friend and now grown into a beautiful corporate executive, suddenly returns to the city, she reenters Jake and Brian's lives and hearts with a vengeance. Sparks fly and an unusual and complicated love triangle ensues.

Rushon is sexually pent-up and ready to take thing things to the next level with his girlfriend, Nikki. But when he calls for a date, she asks to make it a double — bringing along her brash friend, Lysterine, whom Rushon sets up with his lewd buddy, Bunz. Things go better than expected. As the evening transitions from the restaurant to the bedroom, the two men go on a madcap search for what will surely make the night complete: condoms.

Nora Wilder is freaking out. Everyone around her is either in a relationship, married, or has children. Nora is in her thirties, alone with job she's outgrown and a mother who constantly reminds her of it all. Not to mention her best friend Audrey's "perfect marriage". But after a series of disastrous dates, Nora unexpectedly meets Julien, a quirky Frenchman who opens her eyes to a lot more than love.

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.

Mary, a writer working on a novel about a love triangle, is attracted to her publisher. Her suitor Jimmy is determined to break them up; he introduces Mary to the publisher's wife without telling Mary who she is.

Daisy Kenyon is a Manhattan commercial artist having an affair with an arrogant and overbearing but successful lawyer named Dan O'Mara. O'Mara is married and has children. Daisy meets a single man, a war veteran named Peter Lapham, and after a brief and hesitant courtship decides to marry him, although she is still in love with Dan.

Ruth and her beautiful sister Eileen come to New York's Greenwich Village looking for "fame, fortune and a 'For Rent' sign on Barrow Street". They find an apartment, but fame and fortune are a lot more elusive. Ruth gets the attention of playboy publisher Bob Baker when she submits a story about her gorgeous sister Eileen. She tries to keep his attention by convincing him that she and the gorgeous, man-getting Eileen are one and the same person.

Publishing assistant Brett Eisenberg wants to be a big-time editor. However, she lacks self-confidence, a problem that isn't helped by her new, overbearing boss. Brett soon enters into a relationship with Archie, an older man who has plenty of his own issues, including alcoholism, diabetes and a difficult relationship with his daughter. Intent on helping Archie get past his problems, she turns to her dying father for advice.

Romantic comedy about six of Seattle's young people, most of whom live in the same apartment building and whose lives revolve around the city's ever-expanding music scene. The interrelated stories about each character's progress through the singles scene are intriguing and often very funny, and the soundtrack is a grunge fanatic's dream, with the likes of Soundgarden, Pearl Jam and Mudhoney.

Awkward, isolated and disapproving of most of the people around her, a precocious 19-year-old genius is challenged to put her convictions to the test by venturing out on to the NYC dating scene.

In Greenwich Village in the early 1960s, gifted but volatile folk musician Llewyn Davis struggles with money, relationships, and his uncertain future.

On the outskirts of Brooklyn, Frankie, an aimless teenager, suffocates under the oppressive glare cast by his family and a toxic group of delinquent friends. Struggling with his own identity, Frankie begins to scour hookup sites for older men.

Jessica leaves her upper class home to assume an anonymous working class identity. She meets a blue collar guy, Chet and falls in love with the poor but ambitious man. Chet observes a series of suspicious, clandestine meetings with her rich father and his chauffeur which makes him think she is stringing along a "Sugar Daddy" on the side. Financial trickery and sequences of misunderstandings and coincidences culminate with a wedding that turns out much differently than planned.

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.

When famed photographer Christina Eames dies unexpectedly, she leaves her estranged daughter, Mae, hurt, angry and full of questions. When Mae finds a photograph tucked away in a safe-deposit box, she soon finds herself delving into her mother's early life -- an investigation that leads to an unexpected romance with a rising journalist.

This rock opera tells the story of one year in the life of a group of bohemians struggling in late 1980s East Village, New York, USA. The film centers around Mark and Roger, two roommates. While a tragedy has made Roger numb to new experiences, Mark begins capturing their world through his attempts to make a personal movie. In the year that follows, they and their friends deal with love, loss, and working together.

After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.

A New York schoolteacher hits a midlife crisis when, in quick succession, her husband leaves, her adoptive mother dies and her biological mother, an eccentric talk show host, materializes and turns her life upside down as she begins a courtship with the father of one of her students.

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.

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.

A 29-year-old lawyer and her lesbian best friend experience a dramatic shift in their longtime bond after one enters a serious relationship.

Jonathan 'Jack' Harris is a waiter, who hopes to start a newspaper called The Tribeca Times, after the part of Manhattan where he lives, and while struggling to find advertisers and stories decides to do one on Internet dating services, so he joins one and seems to have found a great match, maybe even a soul-mate. He doesn't know it's actually his apartment block neighbor, 29-year old magazine editor Samantha Feld -who only rolled into the thing because her friend and co-worker Jen thinks she needs a man and threw a party at Samantha's place- with whom he clashed from the start in daily life as they consider each-other noisy and inconsiderate. Yet, when they meet after e-mail bliss together and nothing but failed dates with others...

When the fiancé of a fireman reluctantly agrees to participate in a ménage à trois with another woman, she does so on the condition that he reciprocate the favor with another man, which ultimately puts their impending marriage in jeopardy.

Todd's life takes a turn when his friendship with a homosexual causes everyone in his life to start questioning his sexuality.

Piper Grant moves to New York for a fresh start and to find her career passion. As she bounces between different exciting temp jobs that take her all over the city, she meets Austin Edwards, an aspiring writer. While Piper’s sunny optimism is at odds with Austin’s jaded personality, the magic of the autumn season soon brings them closer together. When Piper realizes her true passion is illustration, they decide to team up on a children’s book project, and in the process, they discover the thing they’re really searching for might be each other.

When editor Jane Grant receives a plus-one invitation to her cousin's wedding, she finds herself in a predicament. To one-up her old high school rival Natasha Nutley, Jane tells her about her perfect, charming and handsome boyfriend -- except he isn't real. Catching word of her "boyfriend," Jane's intrusive Aunt Ida demands he make an appearance at the wedding. Now, Jane must go on every date she can snag to find a man who fits the bill.

Susan is a professional flautist who has been handicapped since childhood and is forced to wear a leg brace to get around. After breaking up with her boyfriend, she accepts the offer to travel to Europe on a concert tour. While in Paris, she comes up with an idea to disguise her leg by putting it in a cast and travel on her own to the French Alps to be treated without pity. Not looking to find romance, Susan however has become the interest of Peter, a news photographer. They soon fall in love and Susan is forced to decide if she should tell Peter the truth about herself.

Susan is a newspaper staffer who decides to generate some Christmas spirit by writing an article about her family’s storied 100-year-old, hand-carved, heirloom Christmas angel. This leads her to accidentally meet Brady, a cute, upbeat artist who insists that he and Susan become fast friends (at least). It turns out that this angel also has the spiritual power to bring people together – as it seems to be doing with Susan and Brady. What’s behind this enchanted ornament? As time moves on, more about this captivating artifact is revealed.

A couple of single adults agree to pose as each others significant other throughout the holidays to keep their meddling families from harassing them, only to find that their feelings for each other are real.