Dynamic Watchlist Hub: Apr 10, 2026

10 Best Movies Like Jake Squared

If you loved Jake Squared, 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 Jake Squared.

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#1
Sidewalks of New York

Sidewalks of New York

2001★ 6.0

Why watch this? A perfect follow-up to Jake Squared for fans of Comedy & Drama. 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...

#2
XX/XY

XX/XY

2002★ 5.8

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

Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later....

#3
Almost Friends

Almost Friends

2017★ 6.3

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

A man in his mid-20s, still living at home with his mother and stepfather, puts all his eggs in one basket: the girl who works at his local coffee shop. The problem is, she has a s...

#4
Landline

Landline

2017★ 6.1

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

A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair....

#5
Enemies, a Love Story

Enemies, a Love Story

1989★ 6.2

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

A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife....

#6
CQ

CQ

2001★ 5.9

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

A young filmmaker in 1960s Paris juggles directing a cheesy sci-fi debacle, directing his own personal art film, coping with his crumbling relationship with his girlfriend, and a n...

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