Dynamic Watchlist Hub: May 08, 2026

10 Best Movies Like How to Date Billy Walsh

If you loved How to Date Billy Walsh, 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 How to Date Billy Walsh.

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#1
Playing It Cool

Playing It Cool

2014★ 5.9

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

A young man meets and instantly falls in love with an engaged woman....

#2
Desperados

Desperados

2020★ 6.0

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

A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caug...

#3
Secret Admirer

Secret Admirer

1985★ 6.7

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

An anonymous love letter left in Michael Ryan's locker on the last day of school wreaks havoc on his life and the lives of everyone who comes in contact with it....

#4
Two Can Play That Game

Two Can Play That Game

2001★ 6.4

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

Corporate overachiever and all-around fly chick Shanté Smith thinks she's got the goods to keep her slickster boyfriend Keith, from straying—until he discovers a greener pasture, S...

#5
Someone Great

Someone Great

2019★ 6.4

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

An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and...

#6
Dean

Dean

2016★ 5.8

Why watch this? A perfect follow-up to How to Date Billy Walsh 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...

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