Best Enemies-to-Lovers Movies and Shows You Must Watch

The enemies-to-lovers trope is a favorite in the world of movies and TV shows, offering thrilling dynamics and irresistible chemistry between characters who start off on the wrong foot. To make your viewing experience even better, consider subscribing to Amazon Prime Video. With your Prime membership, you gain access to a vast library of movies and TV shows, including new releases, classics, and exclusive Amazon Originals. Enjoy not only your favorite genres but also Thursday Night Football and more popular content. Plus, you can subscribe to 100+ channels and get special deals to rent or buy new release movies. Not yet a Prime member? Start your 30-day free trial today and experience all these benefits.

 



Here are some of the best enemies-to-lovers movies and shows you must watch, complete with descriptions and links to where you can stream them:


1. Pride and Prejudice (2005)

This adaptation of Jane Austen’s classic novel stars Keira Knightley as Elizabeth Bennet and Matthew Macfadyen as Mr. Darcy. Their initial disdain for each other slowly transforms into deep affection, making it a timeless example of the enemies-to-lovers trope. Watch on Amazon Prime

2. 10 Things I Hate About You (1999)

A modern adaptation of Shakespeare’s “The Taming of the Shrew,” this teen romantic comedy features the fiery relationship between Kat Stratford (Julia Stiles) and Patrick Verona (Heath Ledger). Their initial antagonism turns into a heartfelt romance. Watch on Disney+ or Amazon Prime

3. Bridgerton (2020-)

This hit Netflix series follows the high society drama of Regency-era London, including the sizzling romance between Daphne Bridgerton (Phoebe Dynevor) and Simon Basset (Regé-Jean Page). Their fake courtship turns into a passionate love story. Watch on Netflix or Amazon Prime

4. You’ve Got Mail (1998)

In this charming romantic comedy, bookstore rivals Kathleen Kelly (Meg Ryan) and Joe Fox (Tom Hanks) unknowingly fall in love with each other over email, despite their real-life animosity. The film beautifully blends humor and romance. Watch on Amazon Prime

5. To All the Boys I’ve Loved Before (2018)

Lara Jean Covey (Lana Condor) and Peter Kavinsky (Noah Centineo) start off with a fake relationship to make their exes jealous, but their initial pretense leads to genuine feelings. This Netflix original is a delightful take on young love. Watch on Netflix or Amazon Prime

6. The Proposal (2009)

Margaret Tate (Sandra Bullock) is a tough, high-powered book editor who forces her assistant, Andrew Paxton (Ryan Reynolds), into a fake marriage to avoid deportation. Their initial dislike for each other gradually turns into romance. Watch on Disney+ or Amazon Prime

7. The Hating Game (2021)

Based on the popular novel by Sally Thorne, this film follows the office rivalry between Lucy Hutton (Lucy Hale) and Joshua Templeman (Austin Stowell). Their fierce competition eventually leads to unexpected love. Watch on Amazon Prime

8. Outlander (2014-)

This historical drama series follows Claire Randall (Caitriona Balfe), a World War II nurse who is transported back to 1743 Scotland. Her initial clashes with Jamie Fraser (Sam Heughan) develop into a profound and enduring romance. Watch on Starz or Amazon Prime

9. The Princess Diaries 2: Royal Engagement (2004)

Princess Mia (Anne Hathaway) is forced into an arranged marriage with Nicholas Devereaux (Chris Pine). Their initial friction and competitive pranks eventually blossom into love. Watch on Disney+ or Amazon Prime

10. Enemies: The Story of a Love Affair (1972)

A classic tale of love and hatred, this film explores the complex relationship between former lovers who find themselves on opposite sides of a conflict. Their journey from animosity to love is deeply moving. Watch on Amazon Prime

11. Gossip Girl (2007-2012)

This popular teen drama series features numerous enemies-to-lovers storylines, most notably between Blair Waldorf (Leighton Meester) and Chuck Bass (Ed Westwick). Their tumultuous relationship is filled with passion and drama. Watch on Max or Amazon Prime

12. The Holiday (2006)

In this heartwarming romantic comedy, Amanda Woods (Cameron Diaz) and Iris Simpkins (Kate Winslet) swap homes for the holidays and each find unexpected love. Iris's relationship with Miles (Jack Black) and Amanda's with Graham (Jude Law) both start with misunderstandings and conflicts. Watch on Amazon Prime

13. Pride and Prejudice (1995)

This acclaimed miniseries adaptation of Jane Austen’s novel stars Colin Firth as Mr. Darcy and Jennifer Ehle as Elizabeth Bennet. Their initially contentious relationship evolves into one of deep mutual respect and love. Watch on Amazon Prime

14. How to Lose a Guy in 10 Days (2003)

Journalist Andie Anderson (Kate Hudson) and advertising executive Benjamin Barry (Matthew McConaughey) each have conflicting motives in their relationship, but their schemes lead to real romance. Watch on Amazon Prime

15. Sweet Home Alabama (2002)

Melanie Smooter (Reese Witherspoon) returns to her hometown to finalize her divorce from Jake Perry (Josh Lucas), but their past animosities resurface and eventually rekindle old feelings. Watch on Disney+ or Amazon Prime

16. Ella Enchanted (2004)

Ella (Anne Hathaway) is cursed to obey every command given to her. Her quest to break the curse leads her to Prince Charmont (Hugh Dancy), and their initial friction turns into love. Watch on Disney+ or Amazon Prime

17. Gilmore Girls (2000-2007)

This beloved TV series includes the memorable enemies-to-lovers storyline between Paris Geller (Liza Weil) and Doyle McMaster (Danny Strong). Their academic rivalry turns into a unique and enduring relationship. Watch on Netflix or Amazon Prime

18. The Ugly Truth (2009)

Abby Richter (Katherine Heigl) and Mike Chadway (Gerard Butler) have opposing views on relationships and love, leading to comedic clashes that eventually spark a romance. Watch on Amazon Prime

19. New Girl (2011-2018)

The dynamic between Jess Day (Zooey Deschanel) and Nick Miller (Jake Johnson) evolves from friendship to romance, with plenty of bickering and humorous conflicts along the way. Watch on Netflix or Amazon Prime

20. Clueless (1995)

A modern retelling of Jane Austen’s "Emma," this film follows Cher Horowitz (Alicia Silverstone) as she navigates high school life and her evolving feelings for Josh (Paul Rudd). Watch on Paramount+ or Amazon Prime

Enjoy these fantastic enemies-to-lovers movies and shows with your Amazon Prime membership, and dive into the captivating journey from animosity to affection.

 


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21. The Big Sick (2017)

Based on a true story, this romantic comedy follows the relationship between Kumail (Kumail Nanjiani) and Emily (Zoe Kazan). Despite cultural differences and initial misunderstandings, their bond grows stronger through unexpected challenges. Watch on Amazon Prime, Max

22. Silver Linings Playbook (2012)

Pat (Bradley Cooper) and Tiffany (Jennifer Lawrence) start off on the wrong foot but gradually find common ground through their struggles with mental health. Their evolving relationship is both heartfelt and humorous. Watch on Amazon Prime, Max

23. Crazy, Stupid, Love. (2011)

Cal Weaver (Steve Carell) and Jacob Palmer (Ryan Gosling) form an unlikely friendship that turns Cal's life around. Jacob’s initial disdain for Cal’s ex-wife Emily (Julianne Moore) evolves into something more meaningful. Watch on Amazon Prime, Max

24. Beauty and the Beast (2017)

A modern retelling of the classic fairy tale, this live-action film follows Belle (Emma Watson) and the Beast (Dan Stevens) as they transform their initial animosity into a deep and abiding love. Watch on Disney+ or Amazon Prime

25. The Office (2005-2013)

The slow-burning romance between Jim Halpert (John Krasinski) and Pam Beesly (Jenna Fischer) is a fan favorite. Their relationship starts with playful teasing and friendly banter, growing into one of TV's most beloved romances. Watch on Peacock or Amazon Prime, Max

26. The Mindy Project (2012-2017)

Mindy Lahiri (Mindy Kaling) and Danny Castellano (Chris Messina) go from colleagues who frequently clash to a couple with undeniable chemistry. Their dynamic is both hilarious and heartwarming. Watch on Hulu or Amazon Prime, Max

27. When Harry Met Sally... (1989)

Harry (Billy Crystal) and Sally (Meg Ryan) start off as friends who can't seem to get along, but over time, their relationship deepens into one of the most iconic romances in film history. Watch on Amazon Prime, Max

28. Anne with an E (2017-2019)

Based on the "Anne of Green Gables" novels, this series follows the spirited Anne Shirley (Amybeth McNulty) and her evolving relationship with Gilbert Blythe (Lucas Jade Zumann), who starts as her rival and becomes her closest ally. Watch on Netflix or Amazon Prime

29. The Vampire Diaries (2009-2017)

Elena Gilbert (Nina Dobrev) navigates a complex love triangle with vampire brothers Stefan (Paul Wesley) and Damon Salvatore (Ian Somerhalder). Elena’s initial distrust of Damon evolves into a deep and complicated romance. Watch on Max or Amazon Prime

30. Romeo + Juliet (1996)

Baz Luhrmann's modern adaptation of Shakespeare’s tragedy stars Leonardo DiCaprio and Claire Danes as the titular star-crossed lovers. Their families’ feud makes their love story both passionate and tragic. Watch on Amazon Prime

31. Moonstruck (1987)

Loretta Castorini (Cher) and Ronny Cammareri (Nicolas Cage) are drawn together despite their initial animosity. Their fiery relationship is filled with passion and unexpected twists. Watch on Amazon Prime, Max

32. Letters to Juliet (2010)

While on a trip to Italy, Sophie (Amanda Seyfried) finds a love letter that leads her to meet the charming but initially brusque Charlie (Christopher Egan). Their journey to reunite lost lovers brings them closer together. Watch on Amazon Prime, Max

33. Mr. & Mrs. Smith (2005)

John (Brad Pitt) and Jane Smith (Angelina Jolie) are a married couple who are unaware that they are both secret assassins working for opposing agencies. Their revelation leads to explosive confrontations and a reignited romance. Watch on Amazon Prime, Max

34. Hart of Dixie (2011-2015)

Zoe Hart (Rachel Bilson) moves to a small Southern town and clashes with the local lawyer, George Tucker (Scott Porter), before their relationship slowly warms into friendship and love. Watch on Amazon Prime, Max

35. Leap Year (2010)

Anna Brady (Amy Adams) travels to Ireland to propose to her boyfriend, but ends up relying on the help of the grumpy Declan (Matthew Goode). Their journey across the Irish countryside is filled with bickering and blossoming affection. Watch on Amazon Prime, Max

36. A Knight's Tale (2001)

William Thatcher (Heath Ledger) and Lady Jocelyn (Shannyn Sossamon) start off as adversaries in this medieval adventure, but their relationship transforms into a romantic one as William proves his worth. Watch on Amazon Prime, Max

37. Castle (2009-2016)

Mystery writer Richard Castle (Nathan Fillion) and detective Kate Beckett (Stana Katic) have a rocky start, but their professional relationship evolves into a deep and engaging romance. Watch on Hulu or Amazon Prime, Max

38. The Good Place (2016-2020)

Eleanor Shellstrop (Kristen Bell) and Chidi Anagonye (William Jackson Harper) start off in a morally complex relationship in the afterlife, but their journey leads them to a profound connection. Watch on Netflix or Amazon Prime

39. The Holiday Calendar (2018)

Abby Sutton (Kat Graham) and Josh Barton (Quincy Brown) have known each other since childhood but clash over their different outlooks on life. The magic of an advent calendar brings them closer together. Watch on Netflix or Amazon Prime

40. The Man from U.N.C.L.E. (2015)

In this action-comedy, CIA agent Napoleon Solo (Henry Cavill) and KGB operative Illya Kuryakin (Armie Hammer) must work together despite their initial antagonism. Their partnership evolves into mutual respect and camaraderie. Watch on Amazon Prime

Enjoy these fantastic enemies-to-lovers movies and shows with your Amazon Prime membership, and dive into the captivating journey from animosity to affection.


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