Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Pretty Problems

If you loved Pretty Problems, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

🏆

Expert Review & Ratings

See our full critical analysis and audience score for Pretty Problems.

View Review →
Advertisement
#1
You Will Meet a Tall Dark Stranger

You Will Meet a Tall Dark Stranger

2010★ 5.9

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

Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with ...

#2
Purple Violets

Purple Violets

2007★ 5.8

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

Patti Petalson is a promising writer, but her marriage and conventional job keep her from her dream. She longs to return to her writing, especially after running into her first lov...

#3
The Other Sister

The Other Sister

1999★ 6.4

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

A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college....

#4
Tall Girl

Tall Girl

2019★ 6.3

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

Jodi, the tallest girl in her high school, has always felt uncomfortable in her own skin. But after years of slouching, being made fun of, and avoiding attention at all costs, Jodi...

#5
Best Man Down

Best Man Down

2012★ 6.7

Why watch this? A perfect follow-up to Pretty Problems for fans of Comedy & Drama. It captures a similar light-hearted atmosphere.

A newlywed couple cancels their honeymoon and returns to the snowy Midwest to make the funeral arrangements for their best man, who died unexpectedly after their ceremony....

#6
Let's Make Love

Let's Make Love

1960★ 6.4

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

When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful...

Advertisement