Dynamic Watchlist Hub: May 12, 2026

10 Best Movies Like You're a Big Boy Now

If you loved You're a Big Boy Now, 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 You're a Big Boy Now.

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#1
My Sassy Girl

My Sassy Girl

2008★ 6.7

Why watch this? A perfect follow-up to You're a Big Boy Now for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman....

#2
Sex Appeal

Sex Appeal

2022★ 6.6

Why watch this? A perfect follow-up to You're a Big Boy Now for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend....

#3
A Nice Girl Like You

A Nice Girl Like You

2020★ 5.8

Why watch this? A perfect follow-up to You're a Big Boy Now for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her...

#4
Little Italy

Little Italy

2018★ 6.6

Why watch this? A perfect follow-up to You're a Big Boy Now for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?...

#5
How to Be Single

How to Be Single

2016★ 6.3

Why watch this? A perfect follow-up to You're a Big Boy Now for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world ...

#6
The Incredible Jessica James

The Incredible Jessica James

2017★ 6.2

Why watch this? A perfect follow-up to You're a Big Boy Now 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....

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