

Similar Films
Movies Like Kissing Jessica Stein
2002·97 min·Dir. Charles Herman-Wurmfeld·★ 6.5
Comedy
Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.
Ranked by shared directors, cast, themes, genre, and era — not just generic recommendations.

Chasing Amy
1997·1h 54m·★ 7.2·Kevin Smith
Themes: bisexuality, lesbianFans also liked

The Great Dictator
1940·2h 5m·★ 8.4·Charlie Chaplin
TMDB recommends

10 Things I Hate About You
1999·1h 37m·★ 7.4·Gil Junger
TMDB recommends

Beverly Hills Cop
1984·1h 45m·★ 7.4·Martin Brest
TMDB recommends

Pillow Talk
1959·1h 42m·★ 7.4·Michael Gordon
TMDB recommends

Send Me No Flowers
1964·1h 40m·★ 7.0·Norman Jewison
TMDB recommends

An American Tail
1986·1h 20m·★ 6.9·Don Bluth
TMDB recommends

Hasee Toh Phasee
2014·2h 21m·★ 6.8·Vinil Mathew
TMDB recommends

Conan O'Brien Can't Stop
2011·1h 29m·★ 7.0·Rodman Flender
Both star Jon Hamm & Jennifer Westfeldt

Keeping the Faith
2000·2h 7m·★ 6.4·Edward Norton
TMDB recommends

Blind Date
1987·1h 35m·★ 6.0·Blake Edwards
TMDB recommends

Friends with Kids
2012·1h 40m·★ 6.1·Jennifer Westfeldt
Both star Jennifer Westfeldt & Jon Hamm

Jayson Bend: Queen and Country
2015·49m·★ 5.8·Matt Carter
TMDB recommends

The Hammer
2007·1h 28m·★ 7.1·Charles Herman-Wurmfeld
Starring Heather JuergensenDir. Charles Herman-Wurmfeld
How Good Is Kissing Jessica Stein?
Ratings across IMDb, Rotten Tomatoes, Metacritic, and TMDB, plus our verdict.
Consensus
6.3Mixed Reviews
Score Breakdown
★ TMDB6.0
★ IMDb6.5
🍅 Rotten Tomatoes (Critics)N/A
◆ MetacriticN/A
The Verdict
Decent, Give It a Shot
Related Collections
Find More