Eternity (2025)
Which love matters more: your first or your last? While many of us debate it, Joan (Elizabeth Olsen) has to live it. Directed by David Freyne, “Eternity” takes place in the afterlife where people who recently died must pick where they want to spend the rest of their immortality. Joan must choose between living with her husband of 65 years, Larry (Miles Teller) or her first husband, Luke (Callum Turner), who died serving in the Korean War. Once Joan reaches the afterlife and sees that Luke waited 67 years for her arrival, she is met with an impossible decision and even greater stress.
With talented performances from Olsen, Teller and Turner, “Eternity” explores what actually makes love meaningful. While there are three main characters, Freyne takes an interesting approach to the overdone love triangle. While Larry and Luke’s desire to be chosen remains, Freyne importantly places Joan as the true leader of the story. Romantic relationships are not being done to her but rather she is actively deciding how to approach them on her terms. Get ready to laugh, cry and scream for eternity.
To All the Boys I Loved Before (2018)
Fake dating, love triangles and sisterhood wrapped in a pretty turquoise and pink bow. Based on the best selling book trilogy from Jenny Han, “To All the Boys I Loved Before” (TATBILB) dives into what happens when private love letters result in real confessions. Susan Johnson’s directorial work centers around Lara Jean’s (Lana Condor) collection of unsent love letters getting sent to her string of crushes, one of which is her sister’s ex-boyfriend and childhood friend.
This Netflix original is widely considered a revival of the romcom, featuring all the classic romcom elements: “witty dialogue, a gripping if slightly implausible plot, raging sexual chemistry between the leads, and a cool parent.” Additionally, TATBILB made waves for Asian-American representation. With Lara Jean’s Korean identity discussed throughout the film, TATBILB has been praised for showing Asian girls are capable of being leads in romance. Touching on friendship, family and dating, TATBILB is a modern romcom staple.
When Harry Met Sally (1989)
Can two good friends stay friends without sex getting in the way? Rob Reiner plays with this question in his 1989 film, “When Harry Met Sally.” Exploring the relationship between Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan), this film is regarded as one of the best romcoms of all time. Despite being released almost 40 years ago, “When Harry Met Sally” is still widely watched today.
With the passing of Rob Reiner, many fans are revisiting his filmography and reliving his creative legacy. “When Harry Met Sally” is noted to be one of his greatest works, with the story inspired by him meeting his wife, Michele Singer Reiner. Through meeting his wife, Reiner shifted the original pessimistic tone to be more optimistic and hopeful.
About Time (2013)
Do you want to redo your past awkward moments? Richard Curtis thought the same thing and created his 2013 film, “About Time.” Tim (Domhnall Gleeson) learned the men in his family can travel back in time once they turn 21. With this new discovered talent and a move to the big city, Tim falls in love with Mary (Rachel McAdams). After a missed first meeting, Tim repeatedly travels back in time to meet Mary again and again in order to perfect their love story.
Curtis is no stranger to romcoms, previously directing “Notting Hill,” “Four Weddings and a Funeral” and hit Christmas film, “Love Actually.” What makes “About Time” so special is the extensive study of Tim’s relationships outside of Mary, specifically the bond with his father (Bill Nighy). “About Time” showcases the importance of impermanence and encourages viewers to rethink their mistakes as blessings in disguise.
The Princess and the Frog (2009)
Disney has a movie for every occasion, and Valentine’s Day is no different. Although there is a plethora of Disney romances to choose from, “The Princess and the Frog” is a standout for emphasizing independence, compromise and community. Anika Noni Rose voices Tiana, a hardworking waitress from New Orleans, saving up to open her own restaurant in honor of her late father. Alongside Tiana is Prince Naveen (Bruno Campos), a spoiled and eccentric royal prince visiting Louisiana. When Tiana and Naveen turn into frogs by Dr. Facilier (Keith David), they must travel through the bayou to reverse the curse.
Directed by Ron Clements and John Musker, “The Princess and the Frog” showed young girls to stand up for their dreams. Tiana put her ambitions first and never dimmed her light to please a love interest. Instead, Tiana influenced Naveen to work hard himself and learn basic skills like cooking. On the flipside, Naveen shows Tiana how to have fun and unwind from her high expectations. The romance between Tiana and Naveen displays the importance of balance and not sacrificing yourself for the sake of romance.
The Half of It (2020)
Marking her return to directing after a 15-year hiatus, Alice Wu’s “The Half of It” investigates love while exploring queer identity, Asian-American family relationships and personal limits. The 2020 film stars Leah Lewis as Ellie Chu, a Chinese-American living in the fictional town of Squahamish who writes other people’s essays for a quick buck. Ellie gets approached by Paul Munsky (Daniel Diemer) for her help, but not on the traditional assignment. Paul wants to impress his crush, Aster Flores (Alexxis Lemire) and needs Ellie’s help writing the perfect love letter. Although hesitant, Ellie agrees and finds an unexpected friendship between her and Paul. However, things begin getting messy when Paul learns Ellie also has feelings for Aster. Two friends yearning for the same girl and stuck in a small town, “The Half of It” is a fun spin on the typical romcom structure.
While romance is present, the beauty of Wu’s work lies in Ellie’s path to understanding herself. With college approaching, her queer identity unexplored and living with a single father, Wu encourages the audience to be bold and brave with their life choices.
People We Meet on Vacation (2026)
Continuing the book adaptations is a recent Netflix hit directed by Brett Haley. Based on Emily Henry’s beloved book of the same name, “People We Meet on Vacation” mixes tropical views and complicated relationships for an entertaining wild ride. The film follows Poppy (Emily Bader), a travelling journalist who’s experiencing a writing block that gets invited to Alex’s (Tom Blyth) brother’s wedding in Spain. Having fallen out of touch with Alex, Poppy views this wedding as an opportunity to reconnect with her former friend and gain new journalism material. Spanning across over seven years and multiple vacations,“People We Meet on Vacation” shows the highs and lows of Poppy and Alex’s romantic development.
Demand for romcoms is more present than ever, with this film garnering 17.2 million views over its debut weekend. “People We Meet on Vacation” displays the patience needed in pursuit of love and cements the claim that opposites attract. If you are hungry for more Emily Henry, you’ll be happy to hear this is one of five planned film adaptations. Her books “Funny Story,” “Happy Place,” “Book Lovers” and “Beach Read” are currently in development.
Uptown Girls (2003)
Just because it is Valentine’s Day does not mean you have to solely celebrate romance. Love manifests in multiple forms, and “Uptown Girls” champions honoring your inner child. Molly Gunn (Brittany Murphy) is Lorraine “Ray” Schleine’s (Dakota Fanning) newly appointed nanny. They are polar opposites, learning to get along and from each other. Molly is quirky, naive and frazzled who never held down a job in her life due to her dad’s rockstar status. After getting evicted from her lavish apartment, she takes a job babysitting eight year old Ray. An uptight, hypochondriac with absent parents, Ray butts heads with Molly’s childish nature. Over the course of the film, Molly and Ray develop a deep relationship that sharpens Molly into a responsible adult and allows Ray to embrace being a kid.
Boaz Yakin’s film poses Molly and Ray as two sides of the same coin, as their behaviors are contrasting manifestations from parenting themselves. “Uptown Girls” was originally met with negative reviews but has now been coined a 2000s classic, authentically representing girlhood and female relationships. Additionally, Murphy and Fanning delivered stellar performances that dived into the emotional nuance surrounding loss, friendship and coming of age.
Past Lives (2023)
Stemming from Buddhist history is the Korean term, “inyeon.” Inyeon refers to the fate between two people. As said in the film, “It’s an inyeon if two strangers even walk by each other on the street and their clothes accidentally brush. Because it means there must have been something between them in their past lives. If two people get married, they say it’s because there have been 8,000 layers of inyeon over 8,000 lifetimes.”
Celine Song’s directorial debut is centered around the concept of “inyeon” as she depicts two childhood friends, Nora (Greta Lee) and Haesung (Teo Yoo) over the course of 24 years. Haesung decides to visit Nora and her husband, Arthur (John Magaro) in New York, where the fate of everyone’s relationship is put under a microscope. Song delicately examines the debated topic of fate and destiny. How much of love is inevitable and are we the writers of our story? “Past Lives” tries to answer these questions in a heartwrenching 106 minutes.
Set It Up (2018)
Life gets busy, and therefore, your love life may need a helping hand. Claire Scanlon took this to the next level with “Set It Up,” a romcom taking place in the bustling landscape of New York City. Zoey Deutch and Glen Powell star as Harper and Charlie, two overworked and underpaid personal assistants with overbearing bosses. Hoping to alleviate some authoritative pressure, Harper and Charlie orchestrate their bosses to start a romantic relationship through precise scheduling, secretive gestures and a couple of white lies.
Alongside TATBILB, “Set It Up” has been coined as Netflix’s attempt at the romcom revival. Entertainment Weekly describes the film as, “the gold-standard for the frothy summer romcom” with magnetic chemistry between Deutch and Powell. Love finds itself in unusual places, so keep an eye out the next time you head into the office.
John Tucker Must Die (2006)
For anyone craving a “so bad, it’s good” movie, tune in to “John Tucker Must Die.” When three girls from completely different crowds learn they are dating the same serial cheater, they recruit Kate Spencer (Brittany Snow) to embarrassingly break his heart. Cheerleader Heather Montgomery (Ashanti), academic Carrie Schaeffer (Arielle Kebbel), and hippie activist Beth McIntrye (Sophia Bush) were unaware of each other when John Tucker (Jesse Metcalfe) claimed their relationships must be kept secret during basketball season. Betty Thomas’ playful comedy highlights the power of camaraderie between women and never settling for less.
Thomas’ film was a loose adaptation of a classic Shakespearean story, “The Merry Wives of Windsor.” This followed a common theme of 2000s romcoms being based on Shakespeare’s works. Other well-known examples include: “10 Things I Hate About You,” “Get Over It,” and “She’s the Man.” Much like many other mentioned adaptations, “John Tucker Must Die” spotlighted coming together and not allowing romance to create division in place of community. So, gather your galentines and get inspiration to humble the John Tuckers in your lives.
Theodore Witcher’s first and only directorial work, “Love Jones” is a love letter to the arts, romance and Black talent. Starring Larenz Tate as Darius and Nia Long as Nina, “Love Jones” follows their budding relationship after meeting at a jazz club in Chicago. Striving poet Darius and amateur photographer Nina connect over their affinity for the arts. However, Nina gets invited to New York by her ex-fiance in hopes of fixing their relationship. The film explores the fate of their charismatic bond and fighting for the one you desire.
Along with audience praise, Witcher’s film is listed by Tracee Ellis Ross as one of her five favorite films. She says, “One of the first times I saw myself reflected on screen in a way – just a beautiful story, a love story that felt textured and layered and interesting and beautifully shot, with Black people in the lead positions.” Furthermore, “Love Jones” breaks out of harmful stereotypes about the Black community. Darius and Nina’s relationship is shown outside the context of violence, which was commonly included in many Black films of the time. The producers said, “they wanted to make a modern film about African-American life that did not use violence and recreational drugs as elements in the story.” Overall, “Love Jones” has become a classic appreciated by all audiences.
But I’m a Cheerleader (1999)
What has cheerleading, RuPaul and conversion therapy all in the same place? If you guessed “But I’m a Cheerleader,” you would be correct. Jamie Babbit’s romantic comedy satire focuses on Megan Bloomfield (Natasha Lyonne) getting sent to True Directions, a conversion therapy camp, to “cure” her queerness. However, Megan is in denial about being a lesbian due to not fitting the typical lesbian stereotypes. She is a cheerleader, fairly popular, feminine, and even has a boyfriend despite not being very attracted to him. At True Directions, Megan befriends Graham (Clea DuVall) who helps her come out of her shell, and maybe even the closet.
Babbit investigates heteronormativity, identity and gender roles through a comedic lens. With bright colors and theatrically artificial set design, “But I’m a Cheerleader” visually depicts strict societal binaries for commentary purposes. Since its 1999 release, “But I’m a Cheerleader” remains highly loved to this day, especially by LGBTQ+ audiences. Viewers of all backgrounds can find something enjoyable in Megan’s journey of self-acceptance.
Twinless (2025)
The last movie on this list is one of 2025’s most underrated feature films. Triple threat James Sweeney directed, wrote and starred in “Twinless,” a movie about two strangers meeting at a support group for those who lost their twin. After the death of his twin brother, Rocky (Dylan O’Brien), Rowan attends a support group for twinless twins in an effort to deal with his loss. There he meets Dennis (James Sweeney) and together they grasp being newly alone together. However, there is a unique twist to Dennis’ past that complicates their newfound friendship.
Along with Sweeney’s masterful balancing act, O’Brien captures two individual personalities beautifully in this swirling of genres. From funny to sad and creepy to heartwarming, “Twinless” takes you on paths you would not anticipate. If you are feeling unconventional this Valentine’s Day and want to send indie cinema some love, “Twinless” is your best bet on Feb. 14th.