Dynamic Watchlist Hub: Apr 18, 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
Always Be My Maybe

Always Be My Maybe

2019★ 6.6

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

Reunited after 15 years, famous chef Sasha and hometown musician Marcus feel the old sparks of attraction, but struggle to adapt to each other's worlds....

#2
The Wedding Singer

The Wedding Singer

1998★ 6.8

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

Robbie, a local rock star turned wedding singer, is dumped on the day of his wedding. Meanwhile, waitress Julia finally sets a wedding date with her fiancée Glenn. When Julia and R...

#3
Looking: The Movie

Looking: The Movie

2016★ 7.2

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

Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships ...

#4
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....

#5
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...

#6
Waiting for Forever

Waiting for Forever

2010★ 5.9

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

A Hollywood-set romantic tale of a guy who is content to live his life without a job yet with the love of his life, a young actress....

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