35 Unmissable Rom-Coms – From The 80s’ And Beyond

While it may be pleasant to go against the traditional stereotype of a woman who loves to indulge in the classic rom-com, meet-cute films from the 80s and beyond – make this act nearly impossible.

In an effort to reminisce over the era that once was, here’s a list of the finest love stories to satiate your thirst for romance.

35. The Holiday (2006)


Newly single Amanda (Cameron Diaz) and lonesome Iris (Kate Winslet) spontaneously engage in a ‘home-exchange program’ where the two live in each others’ houses over the course of 2 weeks (whilst during the holiday season). As Amanda lives in Los Angeles and Iris in London, the pair travel across the globe in hopes to celebrate spinsterhood. To their displeasure, romance disturbs their awaited vacation.

34. Leap Year (2010)


Self-driven Anna (Amy Adams), anticipates a proposal from her longtime boyfriend Jeremy (Adam Scott). When asked to spend an evening with him, Anna believes that she must prepare to be asked for her hand in marriage. To her dismay, he presents her with a pair of earrings – claiming no commitment of any sort. Upon his business trip to Dublin, Anna decides to surprise Jeremy and propose herself in order to comply with ancient Irish tradition that allows women to pop the question on leap day. While on her journey however, she develops an unlikely friendship.

33. Life As We Know It (2010)


In an unforeseen turn of events, Holly (Katherine Heigl) and Messer’s (Josh Duhamel) closest friends are struck in a car accident and to their sorrow, die instantly. Upon hearing the tragic news, Holly and Messer’s concern lies with Sophie – the now orphaned child. They soon learn that deceased parents Alison (Christina Hendricks) and Peter (Hayes Macarthur) declared Holly and Messer legal guardians of their child.

32. She’s All That (1999)


Due to his former girlfriend’s infidelity, rising jock star Zach Siler (Freddie Prinze Jr.) sets out to revive his ‘respectable’ reputation. By his peers, he is assigned the daunting task of turning social outcast Taylor (Jodie Lyn O’Keefe) into the prospective prom queen through lessons in elegance, candor, and beauty.

31. The Proposal (2009)


Daunting book editor Margaret Tate (Sandra Bullock) is suddenly struck with deportation to her native country, Canada. In an effort to remain in New York City and continue her career, she enlists assistant Andrew (Ryan Reynolds) as her fiancee – much to his bewilderment.

30. Sweet Home Alabama (2002)


Melanie (Reese Witherspoon) speaks her dreams of fashion design and stardom into existence following the debut of her collection at New York Fashion Week. She also seems to reach the pinnacle of her love life as she is engaged to the city’s most eligible bachelor (Patrick Dempsey). Prior to attaining complete happiness however, she must finalize her divorce to husband Jake (Josh Lucas) – a redneck Alabaman who refuses to grant this wish.

29. Serendipity (2001)


Kate Beckinsale and John Cusack (illustrious names in romantic-comedy) are cast in what cinephiles deem an underrated spin on ‘fling-ship’ and destiny. While their paths collide, a casual meet-cute leads to an adventurous evening spent in New York City. Following the conclusion of their ‘date’, Jonathan (Cusack) suggests that the two exchange contact information, however, Sara (Beckinsale) proposes to leave their fate in the hands of accidental discovery – otherwise noted ‘Serendipity’.

28. He’s Just Not That Into You (2009)


Similar to Love Actually in format, He’s Just Not That Into You provides viewers an insight into the romantic relationships of nine people. The underlying premise relays the idea that while men can be hard to read, women fail to realize that the attraction (from a man’s perspective) is not as deep as they believe.

27. While You Were Sleeping (1995)


Forsaken transit worker Lucy Moderatz (Sandra Bullock) finds solace when admiring her longtime crush Peter (Peter Gallagher) prior to his train to work each day. In an unlikely circumstance, Peter is thrown towards the railroad, leaving him unconscious and in the face of death. As Lucy is witness, she saves Peter and brings him to the hospital where he is declared to be in a coma. While the hospital staff confuse her to be his fiancee, Peter’s family overhears and the perplexity ensues.

26. Hitch (2005)


Alex ‘Hitch’ Hitchens (Will Smith) is noted New York’s ultimate dating coach – providing timid men a chance with the girl of their dreams. A fellow client, Albert (Kevin James) hopes to woo the heavenly Allegra Cole (Amber Valletta), however, doubts his odd personality and average exterior. While helping Albert, Hitch struggles with his own love life following the hard to please Sara Melas (Eva Mendes).

25. Bridget Jones’s Baby (2016)


Once again single, Bridget Jones (Renee Zellweger) finds herself in a ceaseless pursuit to discover love and all its bounties – as people never fail to make her realize. Upon her bachelorette revival, she meets new men while rekindling past flames. In the process, she finds herself unexpectedly pregnant with no knowledge of whom the father may be.

24. How To Lose A Guy in 10 Days (2003)


Ambitious journalist, Andie Anderson (Kate Hudson), proposes an article idea which circulates around the topic of ‘How To Lose A Guy In 10 Days.’ In order to comply with the experiment, Andie notes advertising executive Ben Berry (Matthew McConaughey) as her subject. However, she fails to notice that Ben too, is in cahoots with his colleagues to enthrall Andie and eventually gain himself a reputable client. While Andie aims to steer him away, Ben clings and the two eventually lose sight of the initial goal.

23. Crazy, Stupid, Love (2011)


Cal (Steve Carell) suffers internal conflict once his wife (Julianne Moore) advises that the two get a divorce. While struggling to find a sense of direction, he encounters a fearless womanizer (Ryan Gosling) at his local bar. Upon seeing Cal’s pathetic state, Jacob (Gosling) attempts to reform Cal’s look and ultimately help him approach women.

22. 27 Dresses (2008)


Jane (Katherine Heigl) is the quintessential bridesmaid who never ceases to be there for her friends on their wedding day, and other milestones that may require emotional support. When it comes time for her younger sister to tie the knot, she finds herself in a pickle once discovering her soon to be brother-in-law is coincidently the man she loves. While Jane oppresses her built-up resent for her sister, she happens to butt heads with another man (James Marsden) – an esteemed journalist who happens to be covering the wedding and its preparation.

21. Bridget Jones’s: The Edge Of Reason (2004)


Evergreen spinster Bridget Jones (Renee Zellweger) returns for a sequel to the triumphant film known as Bridget Jones’s Diary. Following the union of Bridget and her one true love, the narrative explores her struggle to maintain a romance whilst growing accustom to a new life. In the midst, Bridget is conflicted when rekindling a friendship with an old flame.

20. The Wedding Planner (2001)


The Wedding Planner captures the soul of a ‘meet-cute’ encounter. Characters Mary (Jennifer Lopez) and Eddie (Matthew McConaughey) happen to share an unlikely run-in that soon blossoms into a whimsical night spent in the park. A few days later, Mary (the wedding planner) sets out to meet her clients and discovers Eddie is one of them. In other words, much to Mary’s dismay – he is soon to be wed.

19. Letters to Juliet (2010)


An aspiring journalist, Sophie (Amanda Seyfried), accompanies her fiancee (Gael Garcia Bernal) on a business trip to Verona, Italy. While sightseeing, she comes across a wall where heartbroken women are known to leave notes to the illustrious Shakespeare heroine – Juliet. While in pursuit of research on the sight, Sophie discovers a 50-year-old letter which was evidently, neglected. Sophie decides to reply and to her surprise, finds the now elderly woman who first wrote the letter – back in the city of Verona in hopes to reunite with her former love and escorted by her ever-so pessimistic grandson (Christopher Egan).

18. Moonstruck (1987)


An Italian-American widower, Loretta (Cher) opts to accept the proposal of wit-less boyfriend Johnny (Danny Aiello). While on a trip to visit his ailing mother, Johnny requests Loretta to invite his younger brother (Nicholas Cage) to the wedding – given their negative relations in the past, he is hesitant to do so himself. In an attempt to get the two to reconcile, Loretta is charmed by Ronny (Johnny’s younger brother) and ultimately lured into the bedroom where he soon declares his love for her.

17. The Big Sick (2017)


Former stand-up comic, Kumail Naninjani creates a screenplay inspired by the occurrence of true events in his personal life. The plot follows the complex relationship between an interracial couple who struggle to understand each other’s differences in culture. Along the way, Kumail reaches an epiphany as to what he believes is important and attempts to relay this newfound honesty to his illiberal family.

16. About Time (2013)


In this film, Tim Lake (Domhall Gleeson) finds himself with the ability to travel through time – a gift evident in his family for generations. Upon discovering this skill, Tim attempts to woo the girl of his dreams (Rachel McAdams) in a series of encounters that do not always go as planned. In the process, he learns that time travel cannot help him escape the ordinary.

15. Jerry Maguire (1996)


Jerry Maguire (Tom Cruise), an earnest man with a lucrative career as a sports agent, soon realizes the immoral nature of the company he works for and happily walks out – following his termination. While out on a whim, he decides to launch his own agency and urges his former colleagues to join him. While his peers stare in utter embarrassment for Jerry, single mother Dorothy (Renee Zellweger) decides to accompany him in an unexpected twist.

14. Love Actually (2003)


Love Actually consists of an ensemble cast, and hence entices film enthusiasts to watch. Aside from the troupe, however, the story is peculiar in that it explores the relationships of nine different couples. Individually, the characters share a relation in one way or another, thus contributing to the overarching plot to find love.

13. Crazy Rich Asians (2018)


In a modern approach to romantic-comedy, Crazy Rich Asians considers the relationship between fellow New Yorker, Rachel Chu (Constance Wu), and Asian-Brit, Nick Young (Henry Golding). As the two are committed to one another, Nick encourages Rachel to accompany him to his best friend’s wedding in native country, Singapore. Upon her arrival, she discovers that the ‘Youngs’ are in fact a reputable family who are known to live a life of luxury. In efforts to build a connection with his family, Rachel struggles to fit in.

12. 13 Going on 30 (2004)


13 Going on 30 follows the unusual birthday of now 13-year-old Jenna. Jenna, tired of the miserable social structure deemed middle school, hopes to skip this phase of her life and live as an adult. For her birthday, she wishes for just this and finds herself awoken as a 30-year-old. She soon realizes that as her life had progressed, her childhood best friend Matt (Mark Ruffalo) is no longer a part of her life, along with her career and social skills in shambles.

11. Say Anything… (1989)


Say Anything… was among the first rom-coms of its generation to be given immeasurable critical acclaim. The film stars Lloyd Dobler (John Cusack) an ambitious high school graduate, and Diane Court (Ione Skye), the elusive beauty with an exceptional academic career. Upon graduation, Lloyd is determined to take Diane out in hopes to pursue a romance. As her social life throughout high school has been close to non-existent, Diane agrees.

10. Pretty Woman (1990)


To begin the decade, we are introduced to what is now deemed a timeless cast – stars Richard Gere and Julia Roberts. In this particular film, the narrative follows the odd relationship between a prostitute (Roberts) and a wealthy businessman (Gere). Precisely, what began as a request for directions led to the overnight affair in which kept the lonely Edward (Gere) company. Soon, Edward ‘hired’ Vivian (Roberts) as an escort to his societal outings, all whilst gradually enhancing her appearance. Through the process, an unconventional romance unfolds.

9. My Best Friend’s Wedding (1997)


A cinematic classic that sheds limelight on a friendship that is soon followed by romance. Cronies Julianne (Roberts) and Michael (Dermot Mulroney) consider themselves to be each other’s best pals. In fact, the two are quite acquainted in terms of secrecy, family, and everything in between. When Michael reveals the news that he is soon to be wed, Julianne is suddenly struck by the romantic feelings she has for him. Upon hearing his declaration, Julianne makes it her mission to put a stop to the wedding and claim what she believes is rightfully hers – Michael.

8. Four Weddings and a Funeral (1994)


Four Weddings and a Funeral is supposedly what gave Hugh Grant ‘heartthrob’ status as he was the lead in this quintessential British romance. The story is shared from Charles’s (Grant) perspective, who is unfortunately unlucky in love on several accounts. Throughout the tale we witness Charles acquire the role of Best Man in a number of his friends’ weddings, yet sadly finds himself attending each one alone. He has a casual run-in with an American girl (Andie MacDowell) at one of the weddings and is caught off guard by the sudden shine he has taken to her. After a sweet however eventful meeting, the two depart and find themselves reuniting on various occasions over the course of a few years.

7. (500) Days Of Summer (2009)


The creators of (500) Days of Summer adopt a unique approach to storytelling – specifically, a non-linear format. While the sequence is sporadic, as viewers we are given a glimpse into the romantic relationship between Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel) over the course of 500 days. The narrative explores a tumultuous affair that experiences several ups and downs, yet only provides the account of Tom as the story is told from his point of view. This film is eccentric, however realistic for those in real-life relationships.

6. Bridget Jones’s Diary (2001)


32-year old Bridget (Renee Zellweger), finds herself in a so-called ‘mid-life crisis’ as her family and friends begin to question her sanity. They rarely surrender when it comes to the inquiry surrounding Bridget’s past dating history and whether she anticipates marriage in the near future. Through this somewhat ‘coming-of-age’ tale, Bridget records her thoughts regarding men, family, and friends in a diary – which makes for a comical take on romance.

5. 10 Things I Hate About You (1999)


10 Things I Hate About You adopts the ‘edgy teen’ sub-genre of romantic-comedy. The film is centered around Kat, played by Julia Stiles and Patrick (Heath Ledger). Kat and her sister Bianca (Larisa Oleynik) are known around town to have a strict father who does not allow them to date until they are of a certain age. Bianca, 16, who longs to be in a relationship begs her father for a chance at the opportunity – his response is a firm no. However, in an unlikely circumstance, he proposes the condition that once Kat has a boyfriend, so can she. In an effort to let Bianca finally date, a fellow suitor at her school bribes another boy (Ledger) to ask Kat out – eventually leading to a whirlwind of romance involving deceit, foolery, charm, and unexpected love.

4. Notting Hill (1999)


Julia Roberts hit which explores the quaint relationship between the Hollywood luminary, Anna Scott (Roberts), and bookshop owner William (Hugh Grant). Upon a visit to the picturesque town of ‘Notting Hill’, Anna stops by a travel bookshop on the high street where she meets William. With his awkward candor, William attempts to charm Anna whilst keeping ‘cool’ in the presence of a celebrity. After several meetings, the pair spark up a romance, however, attempt to do so in hiding.

3. You’ve Got Mail (1998)


You’ve Got Mail was released upon the emergence of technology, with regards to email specifically. The narrative considers an unlikely friendship, however via email. While the two (Meg Ryan and Tom Hanks) fail to meet in person, their connection remains evident through virtual reality. The tale reaches a point of interest when they physically meet, however are unable to identify one another’s internet persona.

2. Sleepless in Seattle (1993)


In efforts to find his father a wife (following the demise of his former spouse), 8-year-old Jonah calls a radio talk-show which helps advertise this very cause. Annie Reed (Meg Ryan), a fellow listener, seems to find the widower’s (Tom Hanks) remarks endearing and thus begins to question her own relationship with fiancee Walter (Bill Pullman).

1. When Harry Met Sally (1989)


A Nora Ephron definitive which led to the subsequent popularity surrounding romantic-comedies and their everlasting charm. When Harry Met Sally follows the tale of two friends who coincidently become acquainted at different points in life. The two ponder over past relationships and in the process, find themselves drawn to one another. Ultimately, their bond experiences complications as the pair did not anticipate an affair.

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