Film

Kissing Jessica Stein

Name: Kissing Jessica Stein
Genre: Comedy
Released: 2002
Cast: Jennifer Westfeldt, Heather Juergensen, Scott Cohen, Jackie Hoffman, Tovah Feldshuh

Romantic comedy

A witty romantic comedy about Jessica, a perpetually single Jewish copy editor in New York, who answers a personal ad from Helen, an art gallerist curious about women. What begins as an experimental dalliance becomes genuine connection, forcing both to examine their expectations about love, identity, and how neatly life fits into categories. Smart, funny, and surprisingly tender.

TMDb rating

3.0

Should you watch it?

Watch it if you like comedy that finds its laughs in nervous first dates, overbearing mothers and the small humiliations of figuring out what you want.

Skip it if the humour leans on cringe and broad sitcom mugging more than on insight, so if you want sexuality examined in depth, this stays comfortably on the surface.

What it asks of you: A brisk ninety-seven minutes of quick back-and-forth and a light touch rather than heavy drama, with enough attention to catch the awkward silences doing the work.

Not sure? Find tonight's pick in a minute.

If you liked this

Chasing Amy1997

Kevin Smith's sharp, funny exploration of a love triangle that hinges on sexuality, identity, and whether attraction follows neat rules. It shares Jessica Stein's gift for making you laugh while genuinely caring about the characters.

But The '90s references and Smith's particular brand of dialogue haven't aged universally well, and the third act pivots in ways some find heavy-handed.

Imagine Me & You2006

A charming rom-com where a straight woman falls for her florist on her wedding day. It has the same warmth, humor, and emotional honesty as Jessica Stein, plus genuinely likeable characters you want to see happy.

But It's unambiguously sweet in a way that skips some of the messier, more interesting complications the better film grapples with.

Brokeback Mountain2005

A devastating portrait of desire, identity, and the gap between who we are and who we're allowed to be. It's far heavier than Jessica Stein, but shares its refusal to treat same-sex love as a punchline or a problem to solve.

But It's genuinely tragic and will sit with you for days in a very different register than the film you've just watched.

Not sure tonight? Get a pick in a minute, starting from Kissing Jessica Stein

The wildcard

Something you would not have found on your own.

Absolutely Fabulous1992

Both use comedy to explore how women relate to their own bodies, desires, and social expectations, and both are genuinely uninterested in flattering their characters or letting them off the hook.

A British comedy about two aging women navigating friendship, desire, and the gap between who they want to be and who they are. The humor is savage, the affection is real, and the underlying desperation and loneliness ground every joke.

But It's aggressively British, the production values are low, and the sensibility is so broad and arch it can feel impenetrable to people outside its reference frame.

Four Rooms1995

A comedy ensemble piece set in a single night at a hotel, centered on performance, desire, and New York energy. It's anarchic where Jessica Stein is controlled, but shares the same pleasure in smart characters doing funny things.

But It's basically a series of sketches; the structure is experimental and some bits land better than others. It feels very '90s in ways that haven't aged well.

The Kids Are All Right2010

A family comedy-drama about a lesbian couple, their adult children, and the sperm donor who upends their life. It's warm, funny, and genuinely interested in how these people actually feel and relate to one another.

But It aims for crowd-pleasing in the third act, softening some of the tensions that made the first half sharp.

Yes, God, Yes2020

A coming-of-age comedy about a Catholic teenage girl, sexual awakening, and self-discovery. Alice Wu directs with real tenderness; the humor comes from character, not stereotype, and the sexuality feels genuinely exploratory.

But It's very much a millennial nostalgia piece set in the 2000s; the religious component might feel overwrought if you're not receptive to it.

The Object of My Affection1998

Paul Rudd and Jennifer Aniston in a romantic comedy centered on desire, friendship, and the question of whether love neatly follows the gender rules we've assigned it. It's genuinely funny and touching in equal measure.

But It's very much a late-'90s artifact; the tone is softer and less strange than Jessica Stein, which some will find safer but less interesting.

Tootsie1982

Dustin Hoffman as an actor who poses as a woman to get a role. It's hilarious, beautifully constructed, and surprisingly thoughtful about gender, performance, and how attraction works when identity shifts underneath.

But The gender politics, while progressive for 1982, feel dated now; it's ultimately a straight man's fantasy and frames femininity as a costume.

The Watermelon Heist2003

Both films trust comedy to do emotional and character work simultaneously, and both are fascinated by how people present themselves versus who they actually are under pressure.

A South African comedy about con artists and mistaken identity, made by Oliver Schmitz. It's stylish, funny, and finds real wit in the gap between performance and reality, with characters who are resourceful, flawed, and unexpectedly touching.

But It's obscure and regional; the rhythm of the humor is distinctly South African, and the film has aged into a period piece you have to meet on its own terms.

Portrait of a Lady on Fire2019

Where Jessica Stein uses comedy to explore how identity and desire don't fit neatly into categories, Portrait treats that same theme with complete seriousness, showing what happens when two people genuinely see each other.

Céline Sciamma's exquisite film about a portrait painter and her subject falling in love while painting in 18th-century France. It's sensual, intelligent, and treats same-sex desire as something profound and ordinary simultaneously. Pure cinema.

But It's slow, painterly, and almost entirely interior; there's no plot in the conventional sense, and if you need narrative momentum you will find it glacial.