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5 great movies to watch on Valentine’s Day

What better way to get in the spirit of Valentine’s Day than by watching a movie? While none of these movies are set around the holiday, they involve love and romance, two of the key ingredients of Valentine’s Day. If you’re looking for something with a happy ending, you came to the right place.

There are thousands of movies within the romance genre, and we picked out five that you can watch on Valentine’s Day. All five films are available on streaming, so you don’t need to leave your house or pull up your credit card information. Our selections include an airplane romance that just came out in 2024, a defining film from the 1980s, and an underrated rom-com from the 2000s.

Upgraded (2024)

Archie Renaux and Camila Mendes in Upgraded.
Amazon Prime Video

The newest rom-com arriving just in time for Valentine’s Day is Upgraded. Ana (Do Revenge’s Camila Mendes) is an intern who dreams of working at a top art gallery. For that to happen, Ana must start at the bottom of the corporate ladder, with the hope of receiving a recommendation to advance he career. The person whom Ana must persuade is Claire Dupont (Marisa Tomei), a top New York City art director with a reputation for being difficult, à la Meryl Streep in The Devil Wears Prada.

Much to her surprise, Ana is summoned on a work trip to London and receives an upgrade to first class. While enjoying the luxurious seating and complimentary champagne, Ana meets Will (Archie Renaux), and the two flirt for the rest of the flight. When Will mistakes Ana for her boss, she doesn’t correct him and goes along with her new identity. Instead of fessing up, Ana doubles down and poses as her boss as she navigates her new double life. How long can she keep the ruse up before Will discovers the truth?

Stream Upgraded on Prime Video.

She’s All That (1999)

Rachael Leigh Cook and Freddie Prinze Jr.stand next to each other on a beach in She's All That.
Miramax Films

Nothing screams Valentine’s Day more than a cheesy 1990s teen romantic comedy. Enter She’s All That, a modern adaptation of My Fair Lady. Zack Siler (Freddie Prinze Jr.) is the king of his high school. The soccer star is dealt a punishing blow to his ego when his girlfriend, Taylor (Jodi Lyn O’Keefe), dumps him for a reality TV star. With his popularity diminishing, Zack says Taylor is replaceable with any girl in the school.

Hearing this, Zack’s buddy, Dean Sampson (Paul Walker), challenges his friend to transform an ordinary girl into the school’s prom queen. The girl in question is Laney Boggs (Rachael Leigh Cook), an unpopular nerd. Zack accepts and starts to befriend Laney. What begins as a mission eventually becomes a romance, forcing Zack to choose between winning a bet or hurting the person he loves.

Stream She’s All That on Netflix or Pluto TV.

Sixteen Candles (1984)

Molly Ringwald and Michael Schoeffling sit on a table and lean in over a birthday cake.
Universal Pictures

John Hughes is the Michael Jordan of teen comedies. Hughes helmed some of the most iconic coming-of-age films from the 1980s, including Ferris Bueller’s Day Off, Weird Scienceand The Breakfast Club. However, his first directorial debut, Sixteen Candles, is probably his most sincere.

Sam Baker’s (Molly Ringwald) 16th birthday is anything but magical. Sam’s family forgets her birthday because of her sister’s wedding the next day. At school, Sam yearns for the popular senior, Jake Ryan (Michael Schoeffling). Yet, the only boy to give Sam the time of day is a nerdy freshman named Ted (Anthony Michael Hall). Will Sam’s birthday wish to be with Jake come true?

Stream Sixteen Candles on Netflix.

Licorice Pizza (2021)

A girl and boy sit next to each other on a plane.
Metro-Goldwyn-Mayer

Paul Thomas Anderson explores young love in the San Fernando Valley in the Oscar-nominated Licorice Pizza. In 1973, Gary Valentine (Cooper Hoffman), a 15-year-old child actor, meets 25-year-old photographer Alana Kane (Alana Haim) on his school’s picture day. Undeterred by their age difference, Gary asks Alana on a date, which she surprisingly accepts. From there, the two form an unlikely friendship that emerges into a business partnership selling waterbeds.

Over time, Gary wants to be more than friends, but Alana does her best to keep things platonic. As Gary and Alana try to separate, their paths inevitably intersect, forcing the friends to confront their feelings for each other. Licorice Pizza capitalizes on Anderson’s strengths – good writing and an eye for emerging talent – as he pens a nostalgic love letter to his hometown.

Stream Licorice Pizza on Prime Video.

Definitely, Maybe (2008)

Ryan Reynolds cuddles up next to his young daughter.
Universal Pictures

Ryan Reynolds is an excellent action hero, with Wade Wilson in Deadpool being his signature role. Before playing the “Merc with a Mouth,” Reynolds’ was best known for starring in rom-coms from the 2000s. There’s a case to be made that Reynolds is a better romantic lead than a superhero because of his performance in Definitely, Maybe.

After an eye-opening sex education class, Maya Hayes (Abigail Breslin) begs her father, Will (Ryan Reynolds), to explain how he met her mother. Despite going through a divorce, Will reluctantly agrees to explain his relationships with three women (Elizabeth Banks, Isla Fisher, and Rachel Weisz), changing their names so Maya can guess which one is her mother. Reynolds is the perfect leading man in a rom-com, with the looks, charm, and personality to back it up. Maybe after Deadpool and Wolverine, Reynolds can return to his roots and make a rom-com.

Stream Definitely, Maybe on Max. 

Editors' Recommendations

Dan Girolamo
Dan is a passionate and multitalented content creator with experience in pop culture, entertainment, and sports. Throughout…
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