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Underrated Valentine's Day Movies You Need To Watch

At the beginning of every February, Valentine's Day is on the mind of many. Couples of all ages are looking for the perfect way to spend the holiday with their significant others, whether it be a romantic night out or a comfy day inside. Fortunately, there's no absence of romantic stories in the media to indulge in for this special holiday, given the plethora of romance films available on streaming services.

However, it can be easy to find yourself watching the same romantic movies over and over again each year. Whether it's iconic romance dramas like "The Notebook" or "Forrest Gump," it's hard to find yourself surprised and emotional over the same story yet again. Even the greatest romantic comedies like "When Harry Met Sally" or "Crazy Rich Asians" can lose their flavor if they're watched too often. So how can you find the perfect date night movie in a seemingly endless sea of content?

Thankfully, there's no need to worry when these 16 films are easily accessible for movie fans. While some may twist your heart in more ways than one, others make the perfect watch for Valentine's Day. Additionally, some of them may be good movies for single people who don't have a special someone to share the holiday with. What better way is there to spend Valentine's Day than with some of these modern classics that may have passed you by when they first came out? 


Steven Spielberg has one of the most iconic filmographies in cinematic history, with blockbusters like "Jurassic Park," "Raiders of the Lost Ark," and "Jaws," as well as award darlings like "Schindler's List," "Lincoln," and "The Fabelmans." However, one underrated entry from the acclaimed director's library is "Always," which was released in 1989 and reunited Spielberg with his "Jaws" actor Richard Dreyfuss.

"Always" centers on Dreyfuss as Pete, a pilot whose recklessness in the air causes him to accidentally crash-land in a forest. When he comes to, he's greeted by Hap, played by legendary Hollywood icon Audrey Hepburn in her final film role before her death in 1993. According to Hap, Pete has flown too close to the sun and was killed in the crash. Forced to view his life from the outside, Pete ends up helping guide a younger pilot into falling in love with his girlfriend, Dorinda, played by Holly Hunter. 

The film, sadly, didn't live up to the standards of Spielberg's other films at the box office. Though the context of its release may have soured opinions of it at the time, it remains a beautiful and quiet film that stands out over thirty years after its release. It may not have the action of Spielberg's other films, but its romantic qualities make it the perfect underrated watch for Valentine's Day. 

Notting Hill

Recommending a romantic comedy starring either Julia Roberts or Hugh Grant is like recommending an action movie starring Sylvester Stallone or Arnold Schwarzenegger. The two are icons of the genre, with Roberts reigning supreme throughout the '80s and '90s with films like "Pretty Woman" and "My Best Friend's Wedding." Meanwhile, Grant was an easy charmer for rom-com audiences, starring in "Four Weddings and a Funeral" and the ensemble Christmas film "Love Actually."

The two rom-com stars were nevertheless fated to collaborate, which they did in the 1999 comedy "Notting Hill." Hugh Grant plays a London bookshop employee who unexpectedly sparks a romance with Roberts' character, an American celebrity. The film garnered comparisons to the 1953 Audrey Hepburn film "Roman Holiday" and has remained a critic favorite with publications like The Guardian

"Notting Hill" is quite the Valentine's Day classic in the United Kingdom. In 2005, it ranked in the British Film Institute's list of the 100 greatest films. It's a must-watch for fans of romantic comedies, especially viewers who have loved Roberts and Grant in their other films. The two not only have impeccable chemistry, but it's quite stunning to see them prove why they were both the king and queen of the genre throughout the '80s and '90s. 

50 First Dates

By the time "50 First Dates" was released in 2004, Adam Sandler and Drew Barrymore had already proven their romantic-comedy chops. The two actors starred together in the 1998 rom-com "The Wedding Singer," which is often regarded as one of Sandler's best films. Thankfully, the former "Saturday Night Live" star recognized that his chemistry with Drew Barrymore was not to be wasted. However, in Peter Segal's "50 First Dates," their romance would have a steeper hill to climb.

In the film, Barrymore plays Lucy Whitmore, a woman living in Oahu with short-term memory loss. As a result, she forgets the events of every day, which results in quite a predicament for Sandler's marine veterinarian Henry, who falls in love with her one day and becomes determined to win her over, again and again, each day. Though it seems like a doomed romance, it's nevertheless a great vehicle for Sandler to turn on the charm as Henry tries many different ways to get Lucy to remember him. 

Though Robert Ebert would unfavorably compare the film to comedies like "Groundhog Day" and "The Wedding Singer," The Guardian praised Sandler and Barrymore's "undeniable chemistry." Barrymore felt as much according to her autobiography "Wildflower," where she calls Sandler her "cinematic soul mate" (via The Washington Post). They would later reunite for a third time with the 2014 film "Blended," proving their long-time on-screen connection is still strong. 

Valentine's Day

Although most audiences prefer the original ensemble rom-com "Love Actually," several films throughout the 2010s attempted to recapture its magic. One of the better attempts at this was "Valentine's Day," released in 2010 and directed by Garry Marshall. Like "Love Actually," the film consists of over a dozen A-list stars, including Jessica Biel, Jamie Foxx, Bradley Cooper, and Anne Hathaway. It also featured the film debut of singer-songwriter Taylor Swift, who performed the Billboard charting song "Today Was A Fairytale" for the film's soundtrack. 

The film centers on several intertwining stories set in Los Angeles on (you guessed it) Valentine's Day. It went number one at the box office on its opening weekend, beating out other blockbusters like "Percy Jackson & the Olympians: The Lightning Thief" and "The Wolfman" (via Box Office Mojo). Reviews were, predictably, unkind. In one of the nicer ones for the Los Angeles Times, a critic noted that many might find the film amusing albeit lacking in plot or depth. 

Nevertheless, a film this cheesy and sappy may be the perfect choice for a Valentine's Day watch. It's not necessarily horrid enough to warrant a "so-bad-it's-good" status, but it's a lighthearted and earnest romp that will likely get any viewer in the mood for the holiday. Plus, its cast is charming enough that none of them come off as unlikable or difficult to root for.

Liberal Arts

Most audiences know Josh Radnor as the iconic character Ted Mosby from the long-running CBS sitcom "How I Met Your Mother," whose romantic ups and downs drove most of the show's plot. After making his writer-director debut in 2010 with "Happythankyoumoreplease," he followed it up with the 2012 film "Liberal Arts." In the film, Radnor also stars as Jesse, a college admissions officer in his 30s who begins a romance with 19-year-old sophomore Zibby, played by Elizabeth Olsen before her breakout role in the Marvel Cinematic Universe as Wanda Maximoff. 

As one would expect, the age gap between the two creates a huge divide between them. Though the film doesn't necessarily end with a happily ever after for Jesse and Zibby, it does conclude on a positive note as the two recognize the problems with their relationship and move on. It's a refreshingly different kind of ending for a romantic movie, especially one with as likable leads as Radnor and Olsen. In a review for The New York Times, the film was favorably compared to "The Graduate" and praised for its takes on aging, youth, and relationships.

About Time

Richard Curtis had little to prove by 2013, having created some of the most generation-defining romantic comedies of the 2000s. Nevertheless, he exceeded critical expectations with "About Time," which paired Rachel McAdams with Domhnall Gleeson. The film centers on Gleeson's Tim, a man who learns that his family possesses the ability to time travel and re-do events, which he uses to influence his love life. Though he seemingly fails at wooing Charlotte, played by Margot Robbie, he eventually falls for McAdams' Mary and becomes set on making their relationship perfect. 

Surprisingly, "About Time" is not McAdams' first nor last on-screen fling with a time traveler, as she previously appeared in 2009's "The Time Traveler's Wife" with Eric Bana, as well as "Doctor Strange" and its sequel "Doctor Strange in the Multiverse of Madness" opposite Benedict Cumberbatch. However, "About Time" is probably the most sentimental of the four films, as Tim's relationship with Mary challenges his desire to turn the clock back at all, and he decides instead to relish the opportunity to spend every day with her.

Critics felt positive about the romantic chemistry between Gleeson and McAdams. Though it may cause frustration for those obsessed with the logic of time travel, it's nevertheless a pleasant and feel-good watch for a holiday like Valentine's Day that may have couples reminiscing on the journeys that brought them together. 

Sleeping with Other People

The genre of raunchy romantic comedy has had its ups and downs in the world of cinema. Films like "When Harry Met Sally" popularized the desire from audiences to "have what she's having," so to speak. However, heading into the 2010s, the raunchy rom-com needed a second wind after the staleness of films aspriring to be the next "The 40-Year-Old Virgin" and "American Pie" (via The A.V. Club). Thankfully, writer-director Leslye Headland came to the rescue.

"Sleeping with Other People," which was released in 2015, features the pairing of post-"Community" Alison Brie and post-"Saturday Night Live" Jason Sudeikis. The two play former friends who lost their virginities to each other in college, only to reunite as adults as they experience relationship issues. Brie's Lainey is obsessed with a former college flame, while Sudeikis' Jake struggles to commit to relationships. Deciding it'd be better to stay friends, they become close as they help each other overcome their issues, all the while ignoring the romantic and sexual chemistry between each other.

Of course, most audience members can probably see where this is heading. The two's feelings for each other eventually build as they decide to throw away all their insecurities and pursue something real. It's a solid, albeit sometimes sultry, Valentine's Day movie night pick, though the chemistry between Sudeikis and Brie alone is worth the ride. However, it will definitely change the way you hear the word "mousetrap." 

The Age of Adaline

"The Age of Adaline" is quite an unconventional love story, though it makes for a great showcase of its leading lady, Blake Lively. The actress has had her fair share of on-screen romances worthy of a Valentine's Day watch, such as her iconic run in The CW drama "Gossip Girl." However, many critics showered Lively in praise for her role in "The Age of Adaline," with The Atlantic comparing her to Katharine Hepburn both in style and in demeanor.

In the film, Lively plays the titular Adaline, a young woman who miraculously survives an accident only to discover that she is unable to age past 29 years old. Set in present-day 2014, Adaline attracts the attention of a young man, only to discover that his father, played by Harrison Ford, was a former flame whose marriage proposal she rejected. Suffice it to say, Lively and Ford are marvelous in their roles, with The Guardian even stating that it was one of Ford's best performances in years.

Simply put, "The Age of Adaline" makes a great, heart-wrenching choice for a Valentine's Day movie night, if only to marvel at the performances of both Blake Lively and Harrison Ford. Though its story may seem cheesy and sappy for some, for others it's the exact kind of beautiful, nuanced portrayal of being unable to age that makes it such a compelling story. 

The Lobster

"The Lobster" is an entertaining watch, there's no doubt about that, but it may strike some viewers as an odd choice for Valentine's Day. Directed by Yorgos Lanthimos, the film takes place in a dystopian society, where Colin Farrell's David is forced to move into a hotel where he has a little over a month to find a romantic partner. If he fails, he will be turned into an animal of his choice (hence the film's seemingly random title). It's a film that lends itself to be more quiet and introspective than one would expect, and reviewers were even more surprised by where it goes from there.

Escaping certain death in the hotel, David finds himself amongst a group of loners, where he strikes up a romance with a short-sighted woman played by Rachel Weisz. However, once their illicit affair is discovered by the leader of the loners, Weisz's character is surgically blinded, forcing David to help her escape. The film ends on a dour but oddly romantic note as David gets ready to blind himself to keep something in common with Weisz's character.

In an article analyzing the film's ending, Collider stated that the ending can be seen as upsetting, implying that "the only way to find the true love and companionship [David] desires is to physically disable himself." However, the article also describes it as uplifting, showing the lengths David would go to in order to stay together with the short-sighted woman. 

The Big Sick

Kumail Nanjiani had quite the fortuitous 2010s, rising as a stand-up comedian and gaining recognition by starring in the HBO sitcom "Silicon Valley." However, Nanjiani hit a new level of critical success with the 2017 film "The Big Sick," which he co-wrote with his real-life wife, Emily V. Gordon. The film is a loosely autobiographical depiction of Nanjiani and Gordon's romance, with him playing a comedian named Kumail who falls for Emily, a heckler at one of his shows played by Zoe Kazan.

Though Kumail and Emily collide when she discovers that his family is planning to arrange for him to marry a Muslim girl, their relationship hits an even bigger snag when Emily is put into a medically-induced coma. While watching over her, Kumail meets Emily's skeptical parents, played by Holly Hunter and Ray Romano, with whom he eventually bonds with over the course of Emily's medical stay. Through his growing friendship with them, he begins to realize his flaws as a romantic partner to Emily and, by the time she wakes up, makes an effort to improve.

The Atlantic writes that "The Big Sick" is one of the best romantic comedies to release in the past decade, which seemed to be agreed upon by Oscar voters. The film was nominated for best original screenplay at the 2018 ceremony, though it lost to Jordan Peele's "Get Out." Nevertheless, it proved to audiences that Kumail had leading-man potential before his debut as a Marvel Cinematic Universe superhero. 

Love, Simon

"Love, Simon," released in 2018, is based on a novel by Becky Albertalli, and marks a significant moment in cinematic history. Released in theaters by 20th Century Fox, it was the first major Hollywood studio movie to center on an LGBTQ+ romance (via Independent). The film stars Nick Robinson as the titular Simon, a closeted high schooler who passes as straight to all his friends and family. However, Simon's sexuality is threatened when another student, Martin, discovers his secret and threatens to expose him unless Simon helps set Martin up with his friend Abby.

Stylized like a John Hughes film, "Love, Simon" feels like as classic as it is fresh, featuring an '80s-inspired score featuring artists like Bleachers, The 1975, and Troye Sivan. Reviewers felt the vibe was perfectly captured, with USA Today particularly highlighting Nick Robinson's performance as the film's "emotional rock." It even earned praise from Albertalli, who called it "romantic" and "charming," which makes it the perfect choice for a Valentine's Day watch for any couple. 

The movie, though it wasn't an Oscar contender the year it was released, has led to its own kind of success. In 2020, a spin-off series on Hulu titled "Love, Victor" premiered, following a new set of characters, with Robinson returning as Simon in Seasons 1 and 2. "Love, Victor" is available on both Hulu and Disney+, so even if you've already seen "Love, Simon," the series may be a good Valentine's Day alternative.

Set It Up

Netflix has become a new home for romantic comedies, featuring some pretty stellar additions to the genre's canon. One of them, 2018's "Set It Up," starred Zoey Deutch and Glen Powell, who were immediately hailed as the new queen and king of the romantic comedy. The two first joined forces on-screen in Richard Linklater's "Everybody Wants Some!!" and Deutch has since wowed audiences with performances in films like "Buffaloed" and "Not Okay," while Powell has made high-profile appearances in "Top Gun: Maverick" and "Devotion." 

In "Set It Up," Deutch and Powell play Harper and Charlie, overworked assistants to their tightly-strung bosses, played by Lucy Liu and Taye Diggs, respectively. After bonding over their mutual troubles, they arrange for their bosses to have a meet-cute with each other in the hopes it will lighten their workloads. However, as one would expect from this type of classic rom-com setup, Harper and Charlie eventually begin falling for each other, which results in a now-iconic scene where they drunkenly share a pizza (via Decider). 

"Set It Up" became a huge critical darling for Netflix, as Deutch recalled in an interview, saying, "It spawned this renaissance of the rom-com." Clearly, audiences in the late 2010s were starved for a feel-good romantic comedy and "Set It Up" has become a timeless must-watch for any couple on Valentine's Day.

Always Be My Maybe

The 2019 film "Always Be My Maybe" was a passion project for longtime friends Randall Park and Ali Wong, who co-wrote the film's script with Michael Golamco. "Always Be My Maybe" came off the heels of 2018's groundbreaking Asian-led rom-com "Crazy Rich Asians," furthering a strong trend of Asian-American-led romantic films. However, "Always Be My Maybe" is quite a different beast than any other romantic comedy out there.

The film stars Park and Wong as childhood friends Marcus and Sasha, who have an awkward sexual encounter as teenagers that estranges them. The two reunite as adults but find that the friction has not gone away. This results in one of the movie's more iconic moments, where they go on a double date with Sasha's boyfriend, Keanu Reeves (as himself). While many Internet users have probably seen the memes of Keanu Reeves crying while drinking wine, few probably know that it comes from this memorable moment in "Always Be My Maybe."

As one would expect, things happen to work out for Sasha and Marcus, resulting in yet another romantic comedy from Netflix with a feel-good ending that makes for a great Valentine's Day experience. Be careful not to turn the movie off too quickly, as you'll miss Randall Park serenading the end credits with an original song titled "I Punched Keanu Reeves," which was added late into the film's development (via Billboard).

Someone Great

While Valentine's Day movie nights are often appreciated by couples, not every film lover is lucky enough to find a significant other in time for the holiday. Some may even be reeling from a breakup. Fortunately, there are films perfect for those people as well, such as the 2019 Netflix film "Someone Great." Written and directed by Jennifer Kaytin Robinson, "Someone Great" stars Gina Rodriguez as a young woman spending her last night in New York City with her female friends following a devastating breakup.

The New York Times describes the film as a fascinating, original examination of not only a breakup but of female friendship. Rodriguez is joined by Brittany Snow and DeWanda Wise as her on-screen companions, who have their own relationship issues to sort out. However, the film's emotional core centers on Rodriguez's Jenny and her loss of love with her long-term boyfriend Nate, played by LaKeith Stanfield. 

Some may be more familiar with the ties between "Someone Great" and popular music. The film's title is inspired by an LCD Soundsystem song of the same name (via Rolling Stone), and its usage of Lizzo's song "Truth Hurts" contributed to the song's chart-topping rise on the Billboard Hot 100 (via Entertainment Weekly). The film also inspired the song "Death By A Thousand Cuts" from Taylor Swift's album "Lover," which led Robinson to reveal the movie itself had been inspired by Swift's 2014 album "1989," particularly its closing track "Clean." 

Plus One

Maya Erskine has become well-known in comedy crowds thanks to her Hulu series "PEN15" alongside collaborator Anna Konkle. On the other hand, actor Jack Quaid, the son of Meg Ryan and Dennis Quaid, rose to prominence with his role in the Amazon superhero series "The Boys." However, both actors came together in 2019 for the romantic comedy "Plus One," centering on two best friends who accompany each other to a string of weddings. 

As one would expect, the wedding antics of "Plus One" starts off fortuitous for Erskine and Quaid's Alice and Ben. Alice helps Ben hook up with several single women at various weddings while Ben agonizes over his dad's announcement that he's getting married to his much younger girlfriend. Eventually, Ben and Alice act on their romantic feelings for one another, which leads to more tension and animosity between them, until they finally overcome their emotional barriers to profess their love for one another.

Reviewers praised "Plus One," particularly the performance and charm of Maya Erskine, with The New York Times going as far to say that "every minute Erskine isn't on screen is a minute wasted." Though Variety criticized its typical romantic-comedy beats and patterns, they nevertheless deemed the film a thoroughly entertaining watch thanks to its two leads' chemistry. It's an enjoyable watch for couples on Valentine's Day that may also appeal to single people who struggle to find love — or even best friends who have been avoiding their feelings for each other. 

I Want You Back

In the streaming age, it's easy for movies to fly under the radar and be missed by many audience members who may otherwise love them. That's certainly true of Amazon Studio's 2022 rom-com "I Want You Back," starring comedy veterans Jenny Slate and Charlie Day. Slate and Day play Emma and Peter, respectively, who meet after both experiencing breakups with their long-term partners. Though the premise seems primed for a romantic fling between the two, they become resolved for something much sinister.

Together, Peter and Emma team up to help each other win back their lost loves by sabotaging their new relationships. It leads to many hijinks that fans of Day's previous work in "It's Always Sunny in Philadelphia" and "Horrible Bosses" may be familiar with, while Slate gives off a charming performance that's hard not to fall in love with. Though the film takes predictable avenues through romantic comedy territory, it has an endearing and heartfelt ending that will twist the emotions of any viewer.

Perhaps more so than any other entry here, "I Want You Back" is as run-of-the-mill as a rom-com can get while still being enjoyable, mostly due to its likable and entertaining lead actors, as noted by The New York Times. Even the supporting cast, which includes Gina Rodriguez and Manny Jacinto, are stand-out performers. Though it's far from the most original romantic comedy, it makes the perfect movie to curl up on the couch with your partner to watch.