Dynamic Watchlist Hub: Apr 14, 2026

10 Best Movies Like How To Date Again

If you loved How To Date Again, 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 Again.

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#1
What's Your Number?

What's Your Number?

2011★ 6.5

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

Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening maga...

#2
Play It Again, Sam

Play It Again, Sam

1972★ 7.5

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

A neurotic film critic obsessed with the movie Casablanca attempts to get over his wife leaving him by dating again with the help of a married couple and his illusory idol, Humphre...

#3
About Fate

About Fate

2022★ 7.5

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

Two strangers believe in love but never seem to be able to find its true meaning. In a wild twist of events, fate puts each in the other's path on one stormy New Year's Eve....

#4
Crossing Delancey

Crossing Delancey

1988★ 5.9

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

Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find h...

#5
Love Hard

Love Hard

2021★ 6.9

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

An LA girl, unlucky in love, falls for an East Coast guy on a dating app and decides to surprise him for Christmas, only to discover that she's been catfished. But the object of he...

#6
Starting Over

Starting Over

1979★ 6.4

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

After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher....

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