
Kissing Jessica Stein
2001 · Movie · R · 97 min · ★ 6.0 · 78% critics
A single New Yorker, tired of disappointing dates and family pressure, answers a personal ad and unexpectedly connects with a woman seeking “friendship and possibly more.” As their bond grows, she navigates awkward first steps, shifting expectations, and what she truly wants from love and companionship.
Also known as Les aventures romantiques de Jessica Stein
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Details
- Years
- 2001
- Release date
- 2002-03-13
- Language
- English
- Rated
- R
- Runtime
- 97 min
- Critic score
- 78/100
- TMDB rating
- 6.0/10 (253 votes)
- Box office
- $10,013,424
About
You may enjoy this if you want a smart, gentle romcom about connection, identity, and family expectations, with a slightly unconventional vibe like Saving Face; Not for you if you need a clear-cut, traditional happily-ever-after.
Pros: witty dialogue; charming chemistry; thoughtful relationship questions | Cons: dated attitudes; uneven pacing; divisive ending
Themes
- bisexuality
- blind date
- romcom
- based on play or musical
- dating
- art gallery
- exploring sexuality
- single woman
- gay theme
- lesbian
- jewish
Cast & crew

Jennifer Westfeldt
as Jessica Stein

Heather Juergensen
as Helen Cooper

Scott Cohen
as Josh Myers

Jackie Hoffman
as Joan

Tovah Feldshuh
as Judy Stein

Michael Mastro
as Martin

Carson Elrod
as Sebastian

Jon Hamm
as Charles

David Aaron Baker
as Dan Stein

Esther Wurmfeld
as Grandma Esther
Directed by Charles Herman-Wurmfeld