10 Romantic Comedies with Cheating Characters

Romantic comedies are a genre known for their light-hearted and humorous take on relationships. However, with many movies featuring characters who cheat on their partners, it's clear that the subject of infidelity is a relatable and often entertaining one. Here is a list of ten romantic comedies that delve into the intricacies of love, betrayal, and second chances.

1. Notting Hill (1999)

One of the most heartwarming rom-coms is “Notting Hill,” a film that not only showcases the heights of love but also the lows of infidelity. The romance between Will (played by Hugh Grant) and Anna (Julia Roberts) is torn apart when Will discovers Anna's infidelity. This movie serves as an excellent example of how trust can crumble and how second chances can heal broken hearts.

2. The Big Sick (2017)

Set against the backdrop of a cultural clash between a Pakistani family and American sensibilities, “The Big Sick” explores the truth, forgiveness, and the lengths one can go to for a loved one. Despite the couple’s efforts to maintain a healthy relationship, they face unexpected challenges, including infidelity. The movie portrays how such actions can shatter relationships and the journey towards rebuilding them.

3. Friends with Benefits (2011)

This romantic comedy starring Justin Timberlake and Mila Kunis is a prime example of how love can be simplified to just physical attraction. The premise of a consensual open relationship gradually exposes the complexities and challenges that arise from this setup. The movie’s humorous and insightful take on infidelity and the constraints of monogamy make it a must-watch for anyone intrigued by such themes.

4. Premature (2016)

Based on the Japanese light novel, “Premature” is a heartwarming, often hilarious, and at times, tragic story about love, regret, and second chances. The protagonist, Yor (Kento Yamada), struggles with his feelings for his late wife’s cheater, Akari (Jun Fukuda). The narrative explores how past actions can haunt and how the concept of love and destiny can be redefined.

5. The Proposal (2009)

In “The Proposal,” Sandra Oh and Ryan Reynolds play a stranded businesswoman and a gay man who end up in an uncomfortable situation. However, the movie also uncovers an underlying issue of a secret romantic relationship that is exposed under the stress of their predicament. The film’s comedic elements add a layer of depth to the exploration of betrayal and the fallout from such actions.

6. When Harry Met Sally… (1989)

Ed Helen’s classic romantic comedy, while less about cheating, touches on the age-old question of friendship versus romance. Although the characters don’t cheat, the movie humorously and brilliantly explores the idea that men and women can’t be just friends when they are so sexually attracted to each other. It’s a seminal film in its exploration of the complexities of human relationships.

7. Blue Is the Warmest Color (2013)

This French film, directed by Abdellatif Kechiche, is garnering critical acclaim and an international audience. “Blue Is the Warmest Color” tells the story of a passionate and tumultuous relationship between two women, adored and loathed in the same breath. The movie’s graphic portrayal of infidelity and the pain it causes adds a poignant and authentic touch to the narrative.

8. 10 Things I Hate About You (1999)

This Shakespearean twist on a modern setting features cheating as part of the plot. The story revolves around Patrick Verona’s (Laroy Watt) secret relationship with Bianca Stratford (Juliette Lewis), the sister of Petruchio (Heath Ledger). Her infidelity spurs Patrick to reevaluate his feelings and ultimately forms the plot of the movie. It’s a rousing display of teenage drama and the hubbub of high school romance.

9. Red Tails (2012) - Not a Traditional Romantic Comedy

While “Red Tails” is primarily a war film, it features a romantic subplot involving an interracial relationship and infidelity. The movie explores the challenges faced by the Tuskegee Airmen and showcases how infidelity affects not only the main characters but also the broader community.

10. Serendipity (2001)

In Jamie Lloyd’s whimsical and romantic take on fate, a fifty-year-old man discovers he’s the cause of another man’s infidelity. The film’s celebration of second chances and the magic of coincidences is woven throughout, making it a compelling story of love, forgiveness, and destiny.

These romantic comedies delve deep into the complexities of human relationships, addressing the topic of cheating in varied and nuanced ways. Each film provides a unique perspective on the consequences of infidelity and the journey towards healing and growth.

Conclusion

Romantic comedies often tackle the complex emotions surrounding love and relationships, and the characters who cheat in these films offer a glimpse into the real-life challenges of navigating fidelity and trust. Whether through humor, drama, or tragedy, these films continue to captivate audiences with their compelling narratives and relatable storylines.

Interested in exploring more romantic comedies? Check out these ten standout films that feature cheating characters and their journeys towards redemption.

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