Dynamic Watchlist Hub: May 10, 2026

10 Best Movies Like The Pretty Man

If you loved The Pretty Man, 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 The Pretty Man.

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#1
You Will Meet a Tall Dark Stranger

You Will Meet a Tall Dark Stranger

2010★ 5.9

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

Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with ...

#2
Dark Eyes

Dark Eyes

1987★ 6.6

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

Aboard a ship early in the 20th-century, a middle-aged Italian tells his story of love to a Russian....

#3
Cyrus

Cyrus

2010★ 5.9

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

With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another ...

#4
Sidewalks of New York

Sidewalks of New York

2001★ 6.0

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

The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with sc...

#5
Peace, Love & Misunderstanding

Peace, Love & Misunderstanding

2011★ 5.8

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

A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce....

#6
A California Christmas

A California Christmas

2020★ 6.4

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

With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas....

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