Dynamic Watchlist Hub: May 16, 2026

10 Best Movies Like Kissing a Fool

If you loved Kissing a Fool, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Kissing a Fool.

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#1
I Love You, Man

I Love You, Man

2009★ 6.6

Why watch this? A perfect follow-up to Kissing a Fool for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close e...

#2
The Baxter

The Baxter

2005★ 6.0

Why watch this? A perfect follow-up to Kissing a Fool for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Mild mannered tax accountant Elliot Sherman is what he calls a "Baxter": the kind of calm, unexciting fellow who "wears sock garters" and "enjoys raking leaves." Loved by bosses an...

#3
Keeping the Faith

Keeping the Faith

2000★ 6.1

Why watch this? A perfect follow-up to Kissing a Fool for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

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, on...

#4
She's Funny That Way

She's Funny That Way

2015★ 5.9

Why watch this? A perfect follow-up to Kissing a Fool for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production....

#5
Bachelor Party

Bachelor Party

1984★ 6.3

Why watch this? A perfect follow-up to Kissing a Fool for fans of Comedy. It captures a similar light-hearted atmosphere.

On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends....

#6
Ghosts of Girlfriends Past

Ghosts of Girlfriends Past

2009★ 6.0

Why watch this? A perfect follow-up to Kissing a Fool for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Celebrity photographer Connor Mead lives life in the fast lane, committed to lifelong bachelorhood and simultaneous relationships with multiple women. On the eve of his younger bro...

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