Dynamic Watchlist Hub: May 12, 2026

10 Best Movies Like Gamble on Love

If you loved Gamble on Love, 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 Gamble on Love.

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#1
Brigadoon

Brigadoon

1954★ 6.5

Why watch this? A perfect follow-up to Gamble on Love for fans of Romance. It captures a similar heartwarming atmosphere.

Americans Jeff and Tommy, hunting in Scotland, stumble upon a village - Brigadoon. They soon learn that the town appears once every 100 years in order to preserve its peace and spe...

#2
Winter Love Story

Winter Love Story

2019★ 6.8

Why watch this? A perfect follow-up to Gamble on Love for fans of Romance. It captures a similar heartwarming atmosphere.

When new author Cassie is paired with successful author Elliot on a promotional book tour, she learns to believe in her talent. She also finds truth in the old adage “you can’t jud...

#3
Sailing Into Love

Sailing Into Love

2019★ 6.9

Why watch this? A perfect follow-up to Gamble on Love for fans of Romance. 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...

#4
Roustabout

Roustabout

1964★ 6.0

Why watch this? A perfect follow-up to Gamble on Love for fans of Romance. It captures a similar heartwarming atmosphere.

After a singer loses his job at a coffee shop, he finds employment at a struggling carnival, but his attempted romance with a teenager leads to friction with her father....

#5
Safe Haven

Safe Haven

2013★ 7.2

Why watch this? A perfect follow-up to Gamble on Love for fans of Romance. It captures a similar heartwarming atmosphere.

A young woman with a mysterious past lands in Southport, North Carolina where her bond with a widower forces her to confront the dark secret that haunts her....

#6
Paris, Wine & Romance

Paris, Wine & Romance

2019★ 6.9

Why watch this? A perfect follow-up to Gamble on Love for fans of Romance. It captures a similar heartwarming atmosphere.

Isabella is the ambitious new owner of her family’s Oregon winery whose dream of becoming world-renowned takes a big step forward when she enters a prestigious wine competition in ...

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