14 Movies to Watch on Valentine's Day with Your Situationship

When I think of February 14th the first thing that comes to mind is the lyric from One Less Lonely Girl, “14th of February not one of them spent with you. How many dinner dates, set dinner plates, and he didn't even touch his food. How many torn photographs are you taping back. Tell me that, couldn't see an open door. But no more, If you let me inside of your world, There'll be one less lonely girl.” The next thing I think of is Valentine’s Day, not because I loathe the holiday, but I have never dated anyone or celebrated it in a romantic fashion. My V-Day’s are usually spent with my girlfriends, galentinezing it up with misandrist flare. I never received flowers or chocolates from a potential parter, but my mom has always made me feel extra special on the day, and for that I am eternally grateful. There is absolutely nothing wrong with adoring or fantasizing about the 14th of February, but it is also nice to not have a looming amount of pressure leading up to it.

So in honor of this subjective holiday, allow me to present you 14 Movies to Watch on Valentine’s Day with Your Situationship (or whoever). Whether you are single, taken, “it’s complicated”, or none of the above, here is a list of movies you can watch to mimic that feeling of butterflies on a hot date! Or distract you from the terror that is “modern dating.” Either way make the most of your Valentine’s Day, with good company or riding solo! Grab a drink and get comfortable, because this could get lengthy. Cin Cin let’s begin!

1. Valentine’s Day (2010) on Hulu

It would be a disservice to the people if I didn’t put this film on here, not only because it’s on theme, but it’s genuinely such a fun flick with a killer ensemble cast. If you love movies like He’s Just Not That Into You, Love Actually, or any ensemble rom com- Here you go! Valentine’s Day directed by Garry Marshall. I’m a sucker for a cliche, especially one wrapped in such a pretty bow. Available on Hulu, treat yourself this Valentine’s Day to a classic, starring Jennifer Garner, Ashton Kutcher, Taylor Lautner and Taylor Swift, Jamie Foxx, George Lopez and so many more. “In a series of interconnected stories, various Los Angeles residents wend their way through the highs and lows of love during a single day. As the holiday unfolds, they experience first dates, longtime commitments, youthful crushes and connections to old flames.” Honestly I love this movie for it’s nostalgia and intertwined storylines, not only will you fall in love with the characters but you’ll fall in love with the possibility of love too. There’s a little something for everyone- especially my Twilight fans!

2. Love Lies Bleeding (2024) on Max

Lesbian romance, blood, sweat and tears- what’s not to like?! This Valentine’s Day broaden your horizon and tune into an absolute absurd flick that will eat you’re heart out. Love Lies Bleeding directed by Rose Glass came out last year and did not receive nearly enough credit for it’s thrilling plot, electric cinematography, and undeniable romance! The films follows Lou, a serious introvert who falls hard for Jackie, an ambitious athlete who's heading to Las Vegas to pursue her body-building dream. Their love quickly takes a turn from vigorous to violent as they get pulled deep into the web of Lou's criminal family. Such a fun and exciting movie, starring the lovely Kristen Stewart and Katy M. O’Brian. Seriously though, watch this movie and then recommend it to others.

3. Maurice (1987) on Tubi

Did you find yourself fancying the following queer films? Call Me By Your Name, Portrait of a Lady on Fire, Queer, Brokeback Mountain, Moonlight, Chasing Amy, or Boys Don’t Cry. If so, allow me to introduce you to yet another film about the complexities of coming to terms with your sexuality in a society that does not accept you fully- Maurice directed by James Ivory. I stumbled upon this film, thankfully, during a Hugh Grant binge and I couldn’t have been more pleased. This is a fabulous film about a man who is rejected by his lover, who attempts to come to terms with his sexuality within the restrictiveness of Edwardian society. For fans of academia in cinema such as The Dead Poets Society or The Holdovers, maybe even Saltburn, I think this one is a great pick for you. Such devastation and beauty in the name of love. After you watch this, watch Sirens with Hugh Grant ( no reason I just think they flow nicely together).

3. Possession (1981) on Prime

What’s more lovely and romantic that gruesome gore? No really, I’m asking. As a horror fanatic, I often find the most passionate entanglements exist among the supernatural. Nosferatu, Carmilla, Twilight obviously, True Blood, so on a so forth. I have watched Possession a handful of times now, in awe of it’s cinematography, vibrant use of red… and obvious outfit repeating. This film is truly a cult classic, shocking visuals, suspense that makes your hair stand up on the back of your neck. The film follows Anna who revealed to her husband, Mark, that she is having an affair, and leaves him and their son. After a series of violent altercations between Mark and Anna, Mark hires a private investigator to follow her. Anna slowly descends into madness, and it's clear that she is hiding a much sinister secret. Get possessed by greatness this Valentine’s Day with Possession, Directed by Andrzej Żuławski.

4. Secretary (2002) on Tubi

I love this movie, more than Babygirl, more than The Piano Teacher— Secretary directed by Steven Shainberg is truly a seductive, erotic masterpiece. We have seen a rise in stories about women’s sexual desires and how they exist beyond traditional feminine roles in society, especially in the bedroom. I love to see exploration of sexuality on screen and when it is done in such a dramatic and colorful fashion like Secretary, how am I to resist. Maggie Gyllenhall and James Spader have such rich, animalistic chemistry that bleeds into the film so beautifully. Lee Holloway, a girl with a history of severe mental health challenges, is released into the care of her parents after returning from a stay at a mental institution. She finds work as a secretary for a stern attorney, E. Edward Grey. However, Lee soon realizes she likes Grey's rigid demeanor more than she’d expected, and begins a sadomasochistic relationship with him. If you enjoy any kind of secret sensual stories, this one is especially for you!

5. Bones and All (2021) on Peacock

My all time, number one, true romance- Bones and All directed by the lovely Luca Guadagnino. This movie left a hole in my heart after I saw it for the first time in theaters, and no amount of time can seem to repair it. After seeing the movie several times and reading the book I find that using cannibalism as a metaphor for intense desire, love, passion that is all-encompassing is so fascinating to me; especially in Ethel Cain’s album Preacher’s Daughter. This film has some of my favorite shots ever, I love the coming-of-age journey and self-discovery of Taylor Russel’s character in tandem with the connection to Timothee Chalamet, beyond their likeness. Maren, abandoned by her father, embarks on a thousand-mile journey through the backroads of America where she meets a few strange fellas with a similar gift of smell. On her exploration she quickly comes to terms with her unfortunate family, her love, and her future. If you have not seen this yet you truly are so lucky, and if you have watch it again!

6. In the Mood for Love (2000) on Max

Speaking of all-encompassing passion, I’m sure you’ve heard of this glorious masterpiece, In the Mood for Love directed by Wong Kar-Wai. This film is not only a masterclass in production and costume design; riddled with rich and vibrant colors, fascinating shapes and textures laced into the wardrobe. The cinematography in this film will have your mouth watering… can you tell I love it or what? The first time I saw this movie, in college, I was just absolutely enamored by the sensuality and chemistry between Tony Leung Chiu-Wai and Maggie Cheung Man-Yuk. Following their characters in 1962 Hong Kong, these two neighbors form a strong bond after both suspect extramarital activities of their spouses. Adultery is may be a sin, but how can a sin look this good? Watch this on Valentine’s Day and remind yourself that love is out there and it may be right around the corner. Or perhaps after seeing this movie you’ll be so love-struck and emotional you’ll break up with your lame boyfriend who lacks motivation and passion… here’s to hoping! Allow yourself to sit back and enjoy this masterpiece, it will definitely put you in the mood!

7. Blue Valentine (2010) on Prime

   To contrast the burning red hot passion we just spoke about, how about something blue? Not only is this film blue in hue, but the subject matter is as well. In Blue Valentine directed by Derek Cianfrance we watch two people fall in and out of love hard and fast- which is exactly how the gut punch feels once the movie ends and the credits roll. This is such a raw story, it feels like watching someone you know, the someone being Ryan Gosling and Michelle Williams; Dean and Cindy. They appear to be living the dream smitten with one another. However, his lack of motivation and her selfish nature force their marriage apart. If you yourself are a skeptic of true love and romance, this may be for you. A story about the reality of settling for what you think you want, or not knowing when its time to end things (warning this film does have a graphic sexual situation). This film shines a beautiful life on the mundane, while making it appear extraordinary- coated in blue.

   
   

   

   
   

8. Death Proof (2007) on Hulu

   Galentine’s Day is arguably more valuable in my opinion than the tradition of Valentine’s Day. Galentine’s is a day, or evening, dedicated to hanging out and celebrating your girl friends and sisterhood. Nothing brings ladies closer together than a common enemy- especially when that enemy is a man. Have a GNI with your closest girls, and have an night dedicated to the de-centering/ destruction of men with Death Proof, directed by Quentin Tarantino. Revenge never tasted so sweet, when Austin’s hottest DJ, Jungle Julia’s plans to hang with her girlfriends is interrupted by an odd old man stalking their night from behind the wheel of his muscle car. This film is full of twists and turns, a true Tarantino classic with the perfect costume and sound design. These girls fight back, and so should you!

   
   

   

   
   

9. Bottoms (2023) on prime

   Have you ever had a crush so severe you started an entire club to get their attention and try to hookup with them? Me neither but in high college I did go out of my way to garner the attention of my long-term crush; he repulses me now. If hopeless romance, raunchy-comedy, sexual innuendos, Rachel Sennott, Ayo Edebiri, and Ruby Cruz excite you as they do me, here is Bottoms directed by Emma Seligman. We’ve all been looking for that timeless 90s-2000s comedy that is absurd, hilarious, and well-lit, and it’s been here. Following two lame best friends PJ and Josie who start a high school fight club to meet girls and lose their virginity. A genius plan that couldn’t go wrong… right? Check it out for yourself, and then afterwards watch Theater Camp too!

   
   

   

   
   

10. Romeo + Juliet (1996) on Hulu

    I figured I had to put a classic on this list, and rather than your typical Old-Hollywood drama, I thought Shakespeare was a better choice. This is one of my top 4 movies of all time, Romeo + Juliet directed by Baz Lurhman- and the movie that made me fall in love with cinema and young DiCaprio. This is a timeless story as we all know, and the modernity of the production design accompanied by the famous iambic pentameter is gold. I am obsessed with the guns in place of swords, the drag, the campiness, everything about this film is perfection. To those hopeless romantic sitting home on Valentine’s Day, the girls who fantasized about the characters on their Honors English reading list, my musical fans, you know who you are. Claire Danes is an icon, she radiates poise and her performance is impeccably theatric and captivating.

    
    
    
    

    

    
    

11. Your Monster (2024) on Max

    This Valentine’s unleash your inner evil. Don’t just spread the love, spread the loath too! Your Monster directed by Caroline Lindy came out last year and I don’t think it got the recognition it deserves. In the same camp as Lisa Frankenstein, Jennifer’s Body, and all things fun and frisky with the supernatural; you don’t wanna miss this. You can read more about it in here, along with killing your demons- or “bad guys”.

    
    

    

    
    

12. Watching the Detectives (2007) Prime

    Lucy Liu and Cillian Murphy, who owns a video store titled “Gumshoe Video” fall in love in the funniest, mysterious way and you have not seen it yet? You haven’t seen this perfect, delightful, amusing flick? Well lucky for you, Watching the Detectives directed by Paul Stoter is on Prime. When I was in high school, and obsessed with Peaky Blinders and Charlie’s Angels, I watched all of Cillian Murphy’s filmography (that I could find) and fell in love with this rom com. Watch as Neil’s world is flipped upside down when he meets Violet and his love for movies and his confused reality becomes more than he can handle. If you have a hot date I wouldn’t recommend watching this with them because you’ll probably end up liking Cillian or Lucy way more, and when you look over and see that bum from Hinge on your couch you’ll wish you watched it alone.

    
    

    

    
    

13. Companion (2025) in theaters

    In theaters this Valentine’s Day is Companion directed by Drew Hancock, starring Sophie Thatcher and Jack Quaid. Since this film is in theaters I will keep it hush hush, but if you want spoilers or have seen this fantastic flick I reviewed it in this weeks Youtube video. When a billionaire’s death sets off a chain of events for Iris and her friends during a weekend trip to his lakeside estate, a lot more is uncovered than she bargained for.

    
    

    

    
    

14. La La Land (2016) on Prime

Finally, are you are a fan of musicals, movies about the movies, or dazzling production design? Have you recently experienced a traumatic heartbreak and wanna relive that icy hot pain? Ya like jazz? La La Land directed by Damien Chazelle, I’m sure you’ve either seen or heard of it already. Believe me guys love to say this is their favorite movie; but then you ask about Babylon and they don’t know about Babylon. This movie is both hopeful and devastatingly hopeless, for the lovers and the dreamers, the romantics and the poets, and those film bro dudes. End your Valentine’s with a crushing beautiful final scene, from a fabulous, crushing movie (with a hilarious scandal at the Oscars).

With that, Happy Valentine’s Day! I hope you enjoy this list and maybe watch a film or two. Whether you are home alone, out on the town, with the company of a lover of all your lovely lads- watch more movies together. Till next time stay flirty, stay thirsty, and stay alert* this holiday. Cin Cin!

See you soon,

Paige B

*Situationships are not real, get out.