Dynamic Watchlist Hub: Apr 12, 2026

10 Best Movies Like 14 Going Steady

If you loved 14 Going Steady, 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 Going Steady.

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#1
XX/XY

XX/XY

2002★ 5.8

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

Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later....

#2
The Best You Can

The Best You Can

2025★ 7.0

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

Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, ...

#3
The Other Sister

The Other Sister

1999★ 6.3

Why watch this? A perfect follow-up to 14 Going Steady for fans of Comedy & Romance & Drama. 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
How to Please a Woman

How to Please a Woman

2022★ 6.3

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

When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself....

#5
Peace, Love & Misunderstanding

Peace, Love & Misunderstanding

2011★ 5.8

Why watch this? A perfect follow-up to 14 Going Steady for fans of Comedy & Romance & Drama. 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....

#6
A California Christmas

A California Christmas

2020★ 6.4

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

With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas....

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