Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like How Not to Propose

If you loved How Not to Propose, 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 Not to Propose.

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#1
Holiday Date

Holiday Date

2019★ 6.5

Why watch this? A perfect follow-up to How Not to Propose for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

When Brooke’s boyfriend, Ethan, breaks up with her just before the holidays, she agrees to go home with Joel, an actor who will pose as her boyfriend....

#2
Valentine Ever After

Valentine Ever After

2016★ 6.3

Why watch this? A perfect follow-up to How Not to Propose for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

Big city girls Julia and her best friend Sydney take a trip to a dude ranch in Wyoming for a fun weekend getaway, but after a brawl at the local bar, the girls are sentenced to sta...

#3
Matching Hearts

Matching Hearts

2020★ 6.5

Why watch this? A perfect follow-up to How Not to Propose for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

As Valentine's Day nears, a matchmaker is tasked by her mentor to find a match for an entrepreneur who believes staying single is the key to success....

#4
Sailing Into Love

Sailing Into Love

2019★ 6.9

Why watch this? A perfect follow-up to How Not to Propose for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

A biology teacher’s crusade to save a nearby island from development leads to unexpected romance with the handsome and mysterious young sea captain who is new to the seaside town o...

#5
Love in the Sun

Love in the Sun

2019★ 6.1

Why watch this? A perfect follow-up to How Not to Propose for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

When successful dating app creator Alana hesitantly gets engaged, she returns to her hometown in Florida to deliver the news to her dad. Upon returning home, she crosses paths with...

#6
All of My Heart: The Wedding

All of My Heart: The Wedding

2018★ 7.4

Why watch this? A perfect follow-up to How Not to Propose for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

Brian and Jenny are planning their wedding at the Inn where they fell in love. When a distant relative arrives and stakes their claim to the Inn, Brian and Jenny must find a way to...

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