Happy Valentine’s Day to everyone who celebrates, and I’d like to extend an even warmer Valentine’s Day message to those who call it a “Hallmark Holiday“. However you may celebrate, it’s always fun to watch a movie that can get you into the spirit of the holiday. Like last year, I’ve compiled a list of two types of films for Valentine’s Day. One list for the couples, and a second list for the single people who still want to enjoy their day!

For The Couples

“I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.“

When Harry Met Sally (1989) dir. Rob Reiner

At the Regal movie theater at MGM Springfield, they’re screening the 1989 Rob Reiner classic, When Harry Met Sally tonight at 6:30. A fun prank I’m pulling on my girlfriend is that I told her we’re going out to dinner, but in reality, we’re going to see When Harry Met Sally. We’ve watched it together before and while I’m a massive fan, she wasn’t too keen to it. Maybe seeing it on the big screen will change her mind.

Nevertheless, When Harry Met Sally is one of my all time favorite films, not just romantic comedies, but films in general. The friends to lovers concept has been done to death, but Reiner does an awesome job slow playing the friendship between Meg Ryan and Billy Crystal for years. As a viewer, you know they’re going to get together, but the anticipation building makes this movie so joyful. That on top of the impeccable fashion sense from both Ryan and Crystal make this an unbelievable Valentine’s flick that also doubles as a top tier autumn film.

Notting Hill (1999) dir. Roger Michell

There are certain films you love. There are certain films you fall in love with. Notting Hill is in the second category. I have fallen in love with the Hugh Grant and Julia Roberts’ starring flick due to its unexpected relationship. Maybe if you’re a guy who is in a relationship with a girl who you deem to be far out of your league, then you should watch Notting Hill. It’s the average guy, who isn’t that average in this because Hugh Grant is handsome, who gets to be with a gorgeous movie star. That doesn’t happen every day. The ups and downs of Notting Hill keep you on your toes and only make you fall further in love with Roger Michell’s romantic comedy.

Crazy, Stupid, Love (2011) dir. Glenn Ficarra, John Requa

One of the funnier comedies of the 2010s has to be Crazy, Stupid, Love. It humorously keeps you alert due to the dynamic comedic timing of Emma Stone, Steve Carell and Ryan Gosling while also touching on the romance you desire. If you’re looking for big laughs and to keep Valentine’s Day light hearted, watch Crazy, Stupid, Love. You’ll receive a ton of humor, cute romance and also be delivered one of the funniest moments of the 2010s when Ryan Gosling, Steve Carell, Emma Stone, John Carroll Lynch, Julianne Moore and Kevin Bacon share the screen.

The Big Sick (2017) dir. Michael Showalter

Michael Showalter brings a three headed monster of romance, tragedy and comedy all together in this romantic comedy that’s perfect for couples on February 14th. He brings the full arc of an early relationship: the meeting, the courting and the falling in love. Past that, we see the unexpected variables of a relationship when tragedy strikes and shows how couples can persevere through the adversity at hand. Kumail Nanjiani comedic aura makes The Big Sick light hearted and his chemistry with Zoe Kazan is second to none.

For The Single Folk

“People don’t realize this, but loneliness is underrated.“

La La Land (2016) dir. Damien Chazelle

There’s a fickle nature of films that cover loneliness mixed with romance. Sometimes they can be misconstrued as love stories gone array. That’s the case of La La Land. Last year when I gave my Valentine’s Day film suggestions, I put La La Land in the category for those with their significant others. I was wrong. This is a film about finding the love of your life, but letting your careers and ambitions tear you apart. You’ll always love that person, but you realize that what you both want is different from each other. In Chazelle’s musical romance, we see a tender ending that harps on that notion of always loving someone and it’s conveyed through a look. It’s sad, but as a viewer, you understand why Gosling and Stone can’t be together.

Past Lives (2023) dir. Celine Song

Right person, wrong time is a classic romantic trope. However, Celine Song imports Korean folklore to enhance that idea with Past Lives. In her directorial debut, she makes a film that rips out your heart and stomps on it. If you’re at the point in your love life where you’ve recently broken it off with “the one”, you must watch Past Lives. It won’t entirely help with your understanding of why it didn’t work, but it’ll hopefully add some levity to the situation through heartbreaking dialogue that left me sobbing in the theater when I saw it in June.

Her (2013) dir. Spike Jonze

From the perspective of Spike Jonze, we see his real life take on his relationship with Sofia Coppola. At least that’s what many people interpret Her as. He just adds a stylistic twist. It’s a film about loneliness that stress the importance of connection and love from another person. Many people may feel content with their loneliness, but having someone to talk to and lean on is important. That’s the message that Jonze is looking to convey.

(500) Days of Summer (2009) dir. Marc Webb

There’s a lot of reasons to watch (500) Days of Summer if you’re single on Valentine’s Day. First off, it includes The Smiths, my favorite band, and they love to sing about misery. We see Joseph Gordon-Levitt’s character bond with Zooey Deschanel’s character over the song There Is a Light That Never Goes Out, and the lyrics aren’t exactly happy; “And if a double-decker bus, Crashes into us, To die by your side, Is such a heavenly way to die, And if a ten ton truck, Kills the both of us, To die by your side, Well, the pleasure, the privilege is mine.”

Going past The Smiths, the non-linear storytelling about a relationship that falls apart is heartbreaking. You’re thrown from days where the two lovers are loving life and thrilled to be with one another. Then moments later, you see Joseph Gordon-Levitt’s character hating the world with dark circles beneath his eyes. And then it’s back to good times. The emotional rollercoaster Marc Webb takes you on hurts at times, but helps you understand the rockiness a lot of relationships harbor.