Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Tricky Business

If you loved Tricky Business, 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 Tricky Business.

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#1
Sex Appeal

Sex Appeal

2022★ 6.6

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

Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend....

#2
He's a Woman, She's a Man

He's a Woman, She's a Man

1994★ 7.0

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

Wing is a devoted fan of popular singer Rose who is involved in a topsy-turvy relationship with her charismatic producer Sam. Willing to go to any length to meet Rose, the willowy ...

#3
Love in the Buff

Love in the Buff

2012★ 6.6

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

When old flames reunite, will it be second time's the charm or a case of once bitten twice shy? Jimmy and Cherie, two ex-lovers from Hong Kong, cross paths in Beijing and can't see...

#4
The Kissing Booth 2

The Kissing Booth 2

2020★ 7.6

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

With college decisions looming, Elle juggles her long-distance romance with Noah, changing relationship with bestie Lee and feelings for a new classmate....

#5
Relative Values

Relative Values

2000★ 6.1

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

A comedy of discriminating taste and dirty little secrets. In 1952 England, Nigel, the Earl of Marshwood, woos Hollywood star Miranda, upsetting both Nigel's mother, Countess Felic...

#6
Bye Bye Love

Bye Bye Love

1995★ 6.0

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

With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has ...

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