Movies like Worth Winning

This romantic comedy involves a high-powered book editor who convinces her assistant to marry her to avoid deportation to Canada, creating a sham engagement scenario much like the protagonist of Worth Winning must navigate. The Proposal delivers on the promised humor of a pretend romance turning real.

This comedy presents a journalist writing an article on how to drive a man away in just 10 days, while the man she chooses is trying to prove he can make any woman fall in love with him. The back-and-forth wagers of How to Lose a Guy in 10 Days resonate with the betting nature and romantic escapades of Worth Winning.

Sweet Home Alabama follows a young woman who must confront her past in the deep south before she can marry in the upscale New York society, combining elements of comedy, romance, and personal growth akin to Worth Winning.

The film delves into the mind of women through the perspective of a man who gains the ability to hear women's thoughts. What Women Want offers a playful and insightful look into relationships and dating, themes also explored in Worth Winning.

Hitch stars Will Smith as a 'date doctor' who helps men win the hearts of women. Audiences who enjoy the love games and strategies in Worth Winning might appreciate the clever and comedic tactics used by the charming protagonist of Hitch to spark romance.

Runaway Bride features Julia Roberts as a woman notorious for running away from the altar, which invites a similar charm and challenge to relationships as depicted in Worth Winning. The dynamic and commitment issues provide plenty of comedy and romance for audiences looking for a similar feel.

Like Worth Winning, The Bachelor is a romantic comedy centered around the concept of marriage and commitment. When a young man learns he must marry by 6:30 p.m. on his 30th birthday in order to inherit a fortune, comedic chaos ensues, echoing the lighthearted, love-centered challenges seen in Worth Winning.

In this movie, a woman applies rules to fix her relationship, but when her boyfriend starts using these rules against her, the love game becomes more competitive. Two Can Play That Game will appeal to viewers who like the strategic, rule-based approach to love as seen in Worth Winning.