Dynamic Watchlist Hub: Apr 12, 2026

10 Best Movies Like 14 That Night

If you loved 14 That Night, 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 14 That Night.

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#1
Love Don't Co$t a Thing

Love Don't Co$t a Thing

2003★ 7.6

Why watch this? A perfect follow-up to 14 That Night for fans of Comedy & Drama & Romance & Family. It captures a similar light-hearted atmosphere.

A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool....

#2
Peace, Love & Misunderstanding

Peace, Love & Misunderstanding

2011★ 5.8

Why watch this? A perfect follow-up to 14 That Night for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce....

#3
Numb

Numb

2007★ 5.9

Why watch this? A perfect follow-up to 14 That Night for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink,...

#4
Rosaline

Rosaline

2022★ 7.1

Why watch this? A perfect follow-up to 14 That Night for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

Left heartbroken after Romeo begins to pursue her cousin Juliet, Rosaline schemes to foil the famous romance and win back her guy in this comedic twist of Shakespeare's Romeo and J...

#5
Cyrus

Cyrus

2010★ 5.9

Why watch this? A perfect follow-up to 14 That Night for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another ...

#6
Mumford

Mumford

1999★ 6.5

Why watch this? A perfect follow-up to 14 That Night for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

When a would-be psychologist, curiously named Dr. Mumford, comes to the idyllic town of the same name and offers his talent for listening and a disarming frankness, the town's quir...

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