Kissing Jessica Stein poster
Where to stream

Kissing Jessica Stein

6.020021h 37mMovieComedy

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.

DirectorCharles Herman-Wurmfeld
WritersHeather Juergensen·Jennifer Westfeldt
ProducersBrad Zions·Eden Wurmfeld

Where to watch

Disney PlusDisney Plus
Availability shown for Canada · rights vary by country

Cast · Directed by Charles Herman-Wurmfeld

JWJennifer Westfeldt
Jennifer Westfeldt
Jessica Stein
HJHeather Juergensen
Heather Juergensen
Helen Cooper
SCScott Cohen
Scott Cohen
Josh Myers
JHJackie Hoffman
Jackie Hoffman
Joan
TFTovah Feldshuh
Tovah Feldshuh
Judy Stein
MMMichael Mastro
Michael Mastro
Martin
CECarson Elrod
Carson Elrod
Sebastian
JHJon Hamm
Jon Hamm
Charles
DBDavid Aaron Baker
David Aaron Baker
Dan Stein
EWEsther Wurmfeld
Esther Wurmfeld
Grandma Esther
HFHillel Friedman
Hillel Friedman
Rabbi
BFBen Feldman
Ben Feldman
Ben Feldman

More from Jennifer Westfeldt · Lead actress

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2005 · 8.2
24
24
2001 · 7.8
This Is Us
This Is Us
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Private Practice
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2007 · 7.5
Numb3rs
Numb3rs
2005 · 7.0
Judging Amy
Judging Amy
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Will Trent
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2023 · 7.3
Childrens Hospital
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Younger
Younger
2015 · 6.9
Two Guys and a Girl
Two Guys and a Girl
1998 · 7.2
See all fromJennifer Westfeldt

More from Charles Herman-Wurmfeld · Director

Legally Blonde 2: Red, White & Blonde
Legally Blonde 2: Red, White & Blonde
2003 · 5.7
The Facts of Life Reunion
The Facts of Life Reunion
2001 · 7.0
The Hammer
The Hammer
2007 · 6.2
Legally Blonde
Legally Blonde
2003 · 5.3
Fanci's Persuasion
Fanci's Persuasion
1995 · 2.6
See all fromCharles Herman-Wurmfeld

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Kissing Jessica Stein — streaming FAQ

Which OTT platform streams Kissing Jessica Stein?

Kissing Jessica Stein is streaming on Disney Plus in Canada, and available to rent or buy on Apple TV Store and Amazon Video. It's not currently on Netflix.

Is Kissing Jessica Stein on Netflix?

No, Kissing Jessica Stein is not on Netflix in Canada as of September 2026. It's currently on Disney Plus.

Is Kissing Jessica Stein on Amazon Prime Video?

Kissing Jessica Stein isn't included with a Prime Video subscription in Canada, but you can rent or buy it on Amazon Video.

Where can I watch Kissing Jessica Stein for free?

Kissing Jessica Stein is available on Disney Plus in Canada, but you'll need an active subscription — there's no free option right now.