Dynamic Watchlist Hub: May 10, 2026

10 Best Movies Like The Five-Year Engagement

If you loved The Five-Year Engagement, 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 Five-Year Engagement.

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#1
The Incredible Jessica James

The Incredible Jessica James

2017★ 6.2

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

Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date....

#2
Jexi

Jexi

2019★ 6.8

Why watch this? A perfect follow-up to The Five-Year Engagement for fans of Comedy. It captures a similar light-hearted atmosphere.

Phil's new phone comes with an unexpected feature, Jexi...an A.I. determined to keep him all to herself in a comedy about what can happen when you love your phone more than all els...

#3
The Ugly Truth

The Ugly Truth

2009★ 6.5

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

A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships an...

#4
Picture This

Picture This

2025★ 6.0

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

Single and without a man on the horizon, Pia runs a failing photography studio in London with her best friend Jay. As her sister Sonal prepares for marriage and her mother Laxmi ur...

#5
Everybody Loves Somebody

Everybody Loves Somebody

2017★ 6.5

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

On the surface, Clara Barron seems to have it all: a job as an OB-GYN; a great house in LA; and a loving family. But, the one thing Clara doesn't have figured out is her love life....

#6
Starting Over

Starting Over

1979★ 6.4

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

After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher....

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