15 Best Date Night Movies of the Last 5 Years, Ranked

The last few years have certainly been tumultuous for the film industry, as the impacts of the WGA strike, the new Screen Actors Guild agreement, the COVID-19 pandemic, and the changes in theatrical distribution have severely impacted the way that audiences consume and experience films. However, romantic films still still have the power to bring audiences together. In fact, there’s no better way to spend time with a fellow film lover than going on a date to see a film.

There have been a number of great romantic films in the last few years that have the potential to be all-time classics. While some are more serious in intent, and others are more serious overall, these films all celebrate the unique challenges and attributes that occur when going on a date with an equally receptive partner. Romantic, funny, and often thought-provoking, these are the best date movies of the last 5 years, perfect to watch with your significant other.

15

‘Anora’ (2024)

Directed by Sean Baker

Anora is not only a great romantic film from indie darling Sean Baker, but a subversive analysis of what the “American dream” is all about. Mikey Madison, who gives a stunning breakout performance following her standout roles in Scream and Once Upon a Time in Hollywood, is emotionally vulnerable to the point that it is nearly impossible not to sympathize with her plight.

The quiet strength of Anora is the terrific performance by Yura Borisov, whose role as the charismatic Russian henchman Igor doesn’t really come into play until the final act. Although a few twists and turns would suggest that Anora is slightly more cynical about romantic fantasies than it initially seemed to be, the emotionally overwhelming finale ensures that viewers will have something to discuss long after the credits close. It’s also quite funny, and one of the more unpredictable independent dramedies in years.

14

‘Cyrano’ (2021)

Directed by Joe Wright

Cyrano is inspired by one of the greatest romantic stories of all time, which has already been adapted to the big screen several times. However, the inventive new take from director Joe Wright reimagines the story as a medieval musical featuring Peter Dinklage in what may be his greatest film role since The Station Agent. The terrific soundtrack by The National is the perfect blend of classical poetry and pop sensationalism.

Wright is a terrific director for period pieces, as he already mastered the World War II era with Atonement and Darkest Hour. Even though Cyrano takes place several centuries earlier, the attention to detail in the costuming, makeup, and production design is simply transporting. While anyone familiar with the story will know that it ends on a tragic note, Cyrano is a reminder that not all love stories are meant to last and that the most powerful ones make the most of the limited time that they are afforded.

13

‘All of Us Strangers’ (2023)

Directed by Andrew Haigh

All of Us Strangers is one of the most devastating tearjerkers in years, and is sure to hit a chord with anyone that has a difficult relationship with their parents. Although the film is painfully accurate in its depiction of loneliness and other mental health issues, the inclusion of an inventive fantastical element allows director Andrew Haigh to tie together the past and present in emotionally devastating ways.

Andrew Scott gives the single greatest performance of his entire career, which is no small statement considering how phenomenal his work in prestige television shows like Sherlock, Fleabag, and Band of Brothers have been. While it was a role that was sadly overlooked for an Academy Award nomination, Scott and the film itself are almost guaranteed to be acclaimed as future classics in the years to come, especially within arthouse film circles.

12

‘Elemental’ (2023)

Directed by Peter Sohn

Elemental is one of the better Pixar films in recent years, and a sign that the studio is still interested in telling original stories. Although Pixar may have released sure fire hits in the form of sequels like Inside Out 2 and Incredibles 2, Elemental was one of the rare films that became a word-of-mouth sensation; despite being initially dismissed as a major financial disappointment, the film overperformed to become one of the bigger family features of 2023.

Elemental tells a compassionate story about love between members of different communities, and can be viewed as a commentary on race, culture, and immigration. Although the weighty themes are enough to ensure that adults have something to think about, the bright colors and goofy humor provide an age-appropriate romantic fable for children that are too young to watch most other entries in the “date night” category.

11

‘The Fall Guy’ (2024)

Directed by David Leitch

The Fall Guy is proof that action films can be very romantic, as this endearing reimagining of the classic television series of the same name is actually one of the more sincerely heartfelt rom-coms in recent memory. Although The Fall Guy’s greatest love affair is the affinity that it shows for the art of stunt performances, the charming chemistry between Ryan Gosling and Emily Blunt offers a sense of star power that has rarely been seen since the Golden Age of Hollywood.

The Fall Guy is quite cheeky with its sense of humor, as it is more than willing to make fun of the state that blockbuster filmmaking has been in for the last several decades. In an era where many action films are dominated by CGI, The Fall Guy is proof that romance, practicality, and great characters are more important to crafting a crowd-pleaser than virtually anything else.

10

‘Flora and Son’ (2023)

Directed by John Carney

Flora and Son is yet another profound combination of music and romance from director John Carney, whose previous films, Once, Begin Again, and Sing Street, perfectly combined the two intentions. Flora and Son centers on a single mother (Eve Hewson) who bonds with a music instructor (Joseph Gordon-Levitt) as she attempts to learn to play guitar.

While the film adds some light doses of comedy, it’s a remarkably insightful portrayal of the challenges of living with a disruptive family. Flora and Son excels with its original music, with new tracks like “Meet in the Middle” and “High Life” serving as a perfect embodiment of the characters and their relationship. It’s a little disappointing that Flora and Son was only released on Apple TV+, as it was clearly a film that could have benefited from being seen alongside a large crowd of movie lovers.

9

‘Compartment No. 6’ (2021)

Directed by Juho Kuosmanen

Compartment No. 6 is a throwback to classic films like Brief Encounter and Roman Holiday, acting as an examination of the love that can emerge in a single day. Finland’s submission for the 2022 Academy Award for Best International Feature, Compartment No. 6 explores the relationship between a European exchange student and a charismatic Russian miner as they bond during an extended train ride.

Compartment No. 6 doesn’t need big, flashy moments to be entertaining, as most of its romantic moments come from great dialogue. The film never goes beyond the confines of the train ride, yet Compartment No. 6 remains engrossing throughout. It will be frankly exciting to see what director Juho Kuosmanen does next, as Compartment No. 6 is a remarkable display of technical and narrative proficiency.

8

‘The Worst Person in the World’ (2021)

Directed by Joachim Trier

The Worst Person in the World is a romantic comedy like no other, as it engages with the idea that someone can feel like a bad person despite making very human errors. Joachim Trier’s relentlessly funny yet undeniably moving film examines a year in the life of Julie (Renate Reinsve), who feels the pressures of anxiety as she reaches her 30th birthday.

Reinsve’s performance is so effortlessly charismatic that it’s very easy to fall in love with her flawed character. The Worst Person in the World doesn’t shy away from serious issues like sexism, disease, addiction, and depression, but Julie is such a hilarious character that the film never feels too dour. A hit with both awards voters and cinephiles, The Worst Person in the World earned Academy Award nominations for Best International Feature and Best Original Screenplay.

7

‘Bros’ (2022)

Directed by Nicholas Stoller

Bros is a great modern romantic comedy that serves as a powerful piece of LGBTQIA representation and addresses many of the issues that are common within that community. Billy Eichner gives a remarkably sensitive performance as Bobby, a self-professed cynic who begins to fall head-over-heels in love with his new crush, Aaron (Luke Macfarlane). While Bobby is an advocate for representation, he finds it hard to actually commit himself to a serious relationship.

Unabashedly sincere, Bros feels like a slightly more mature version of the sardonic romantic comedies that Judd Apatow frequently produced in the early 21st century. Bros is raunchy without being perverse and develops great chemistry between Macfarlane and Eichner. Although seeing the relationship between the two is the main attraction here, Bros also features scene-stealing performances from Jim Rash and Debra Messing.

6

‘Fallen Leaves’ (2023)

Directed by Aki Kaurismäki

Fallen Leaves is a quirky, utterly charming rom-com that perfectly shows how films can bring people together. Finland’s submission for the Best International Feature Oscar follows the relationship between loners Ansa (Alma Pöysti) and Holappa (Jussi Vatanen) as they begin attending regular screenings at a local movie tavern. Despite being less than 90 minutes in length, Fallen Leaves does a great job of exploring the power that art has to make people feel seen.

While it does end on an optimistic note, Fallen Leaves has a very black sense of humor, often making jokes about depression, alcoholism, and isolation. That being said, it’s also more than a treat for movie buffs, as it contains a reference to the bizarre Jim Jarmusch comedy The Dead Don’t Die that will be hilarious to anyone who saw the reviled film.

5

‘Palm Springs’ (2020)

Directed by Max Barbakow

Palm Springs was released at just the right time. Despite receiving rave reviews out of the Sundance Film Festival, the film’s theatrical release was halted because of the COVID-19 pandemic. However, releasing Palm Springs on Hulu proved to be the perfect distraction for bored movie buffs who felt like they were living the same day over and over again. Palm Springs ended up being the best time loop movie since Groundhog Day.

This charming and clever sci-fi rom-com succeeds thanks to the great chemistry between Cristin Miloti and Andy Samberg, two inherently comedic actors who nonetheless get serious when the story calls for it. Time travel movies can easily get way too confusing for their own good, but Palm Springs explains its mythology succinctly, never doing a disservice to the romantic dynamic between the central two characters.

4

‘West Side Story’ (2021)

Directed by Steven Spielberg

West Side Story is one of the best remakes ever made, somehow surpassing the original 1960 Best Picture-winning film. Rather than simply recreating the original classic shot-for-shot, Steven Spielberg and screenwriter Tony Kushner create a modern update that spends more time fleshing out the Puerto Rican characters. The film’s amazing dance sequences are just as exciting as any of the action in Spielberg’s Indiana Jones or Jurassic Park films.

A great date movie for those looking for a healthy dose of Hollywood dazzle, West Side Story gives more nuanced depictions of characters from the original. While Ariana DeBose rightfully earned the Oscar for Best Supporting Actress, Mike Faist also deserves credit for showing a more three-dimensional version of the headstrong character Riff. It’s not only Spielberg’s best film in years but one that introduces iconic music to a new generation.

3

‘Licorice Pizza’ (2021)

Directed by Paul Thomas Anderson

Licorice Pizza is a quirky and highly compassionate throwback film that sheds insight into a very strange relationship. The film centers on 15-year-old aspiring actor Gary (Cooper Hoffman), who begins to fall in love with 25-year-old Alana (Alana Haim) as they go on adventures in the San Fernando Valley throughout the 1970s.

While its an era and location that director Paul Thomas Anderson had explored in his classic films Boogie Nights and Magnolia, Licorice Pizza feels fresh because of its youthful exuberance. It’s a film about how everything can feel more important when one is young and in love. Licorice Pizza doesn’t judge its characters and is willing to show how they are flawed but worth empathizing with. Hoffman and Haim have extraordinary chemistry, but a scene-stealing performance by Bradley Cooper may provide the film with its single most hilarious moment.

2

‘Hit Man’ (2024)

Directed by Richard Linklater

Hit Man subverts everything that audiences may have expected from a con man story and even acknowledges that it is not a traditional biopic by any stretch of the imagination. Richard Linklater’s latest masterpiece focuses on college professor Gary (Glen Powell), who secretly works for the police department by pretending to be a hitman. After Gary falls for the femme fatale Madison (Adria Arjona), he must determine if he can actually be the man he is pretending to be.

As with many of Linklater’s best films, Hit Man features compelling dialogue and coasts on the charisma of its two lead performers. Some moments feel reminiscent of other “first date” classics, giving it a timeless quality. However, Hit Man features a bold and surprisingly thought-provoking ending that is bound to get viewers talking as soon as it ends.

1

‘Past Lives’ (2023)

Directed by Celine Song

Past Lives is an extraordinary examination of rekindling a childhood romance that also serves as an astute look at the immigrant experience and communication within the Internet era. Celine Song’s breathtaking directorial debut focuses on a Korean woman (Greta Lee) who encounters her childhood lover (Teo Yoo) late in life, even though she is happily married to an American husband (John Magaro).

What could have easily been a schmaltzy, superficial love triangle story is instead one of the most profound and intimate romances A24 has ever released. Past Lives takes its time to get to know the characters by observing their everyday lives, allowing the viewer to feel more connected to their decisions. In addition to making a sizeable dent at the independent box office, Past Lives scored Academy Award nominations for Best Picture and Best Original Screenplay.

NEXT: The Best Romantic Movies of All Time, Ranked