Dynamic Watchlist Hub: Apr 19, 2026

10 Best Movies Like Chasing Fifty

If you loved Chasing Fifty, 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 Chasing Fifty.

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#1
Long Weekend

Long Weekend

2021★ 7.0

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

Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chanc...

#2
¿Quieres ser mi hijo?

¿Quieres ser mi hijo?

2023★ 8.5

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

Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship ...

#3
Players

Players

2024★ 6.1

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

New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it take...

#4
Dean

Dean

2016★ 5.8

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

A comedy about loss, grief, and the redemptive power of love. Dean is a NY illustrator who falls hard for an LA woman while trying to prevent his father from selling the family hom...

#5
The List

The List

2023★ 6.0

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

After her fiance sleeps with a celebrity on his free pass list, Abby Meyers, with nothing but five names and a fantasy shared by millions, sets out for Los Angeles to sleep with so...

#6
The Good House

The Good House

2021★ 6.2

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

Hildy Good, a wry New England realtor and descendant of the Salem witches who loves her wine and loves her secrets. Her compartmentalized life starts to unravel as she rekindles an...

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