Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Undateable John

If you loved Undateable John, 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 Undateable John.

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#1
The Baltimorons

The Baltimorons

2025★ 6.2

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

A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together....

#2
Purple Violets

Purple Violets

2007★ 5.8

Why watch this? A perfect follow-up to Undateable John 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
Enemies, a Love Story

Enemies, a Love Story

1989★ 6.2

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

A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife....

#4
Camille

Camille

2008★ 6.2

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

A twisted honeymoon adventure about a young couple on their way to Niagara Falls....

#5
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 Undateable John 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 ...

#6
Irreplaceable You

Irreplaceable You

2018★ 6.9

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

A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating....

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