Culture / Entertainment

The Best Romantic Movies for Valentine’s Day Streaming

From 1980s Classics to Groundbreaking Picks

BY // 02.09.19

With Valentine’s Day around the corner, perhaps like me, you might be in the mood for binge-watching some classic romantic movies. For those of you who have gotten to know me, you likely recall that my cultural reference point is generally all that occurred in the 1980s and moment’s ever since.

Yes, I will likely be chastised for not having movies like Gone With The Wind, Casablanca, and Love Story on my list. But I feel like most folks would likely fall back on those classics if asked anyway.

Hopefully, you will find my thinking a little more out-of-the-box. Below are my suggestions for the best romantic movies.

Sixteen Candles

I couldn’t have a  list without at least one John Hughes films on it. That said, this is perhaps my favorite. The story of a girl turning sweet 16 and pining for the dreamiest boy in school. In unison — Jake Ryan.

If the 1980s were your formative years then you remember his name. He had the hair, the voice, the car and most of all the heart of a romantic. Who doesn’t just die each time when Samantha (Molly Ringwald’s character) and Jake kiss over a candlelit table on his parent’s dining room table.


You might find this choice odd, but I get so giddy every time I watch Clueless due to the fun fashion and snappy one-liners. (Remember: “Do you prefer fashion victim or ensembly challenged?”)


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At its core, this is a love story between Cher and Josh. Albeit, it always creeped me out that they were “technically” brother and sister. If you love this ’90s classic as much as me, then definitely consider heading to the Wheelhouse this Wednesday, February 13 for a Galentine’s Day Cabaret Extravaganza.

Creator and performer Brigham Mosley and director Janielle Kastner will bring their wildly successful “Movies That Should Be Musicals” series to the restaurant with a brand new presentation of Clueless. Selected scenes from the film will be interspersed with live music, dance and hilarious commentary for a cabaret-style musical performance.

So find a fabulous yellow plaid outfit and plan on sipping on the signature cocktails: “The Snob & A Half” and “The Way Harsh Tai.”

Clueless movie
Clueless is a modern classic for a reason.

Brokeback Mountain

I had to have at least one serious film on the list. This amazing love story, based on the novel by Annie Proulx is definitely a tear-jerker. It’s also the first gay-themed movie to be honored with an Academy Award nomination.

In addition to being an amazing love story of two cowboys played by Jake Gyllenhaal and Heath Ledger, it is an incredibly beautiful film. Ang Lee’s canon of work is so incredibly diverse from Crouching Tiger, Hidden Dragon to The Ice Storm. However, Brokeback Mountain is my favorite.

How to Lose a Guy in 10 Days

I saved this for last as I have a story to share. Hopefully, you will find it very inspiring. I lived in Los Angeles in the late 1990s when I was in my twenties. Quite a few friends of mine that I grew up with in Tallahassee had made their way to the Left Coast. I was one of the last to arrive on those sunny shores.

We were all quite poor, working entry-level jobs (me at LACMA, the Los Angeles County Museum of Art). Two of my closest girlfriends, Jeannie Long and Michelle Alexander, realized they would have no money to buy Christmas presents.

They had been inspired for years by those around them who were writing for televisions shows or scripts for movies. The two of them decided to write a book. What about? Well, something they thought they knew lots about — how to chase away men.

They spent months writing the book and finally went to Kinkos to have it printed and bound for holiday gifts. Michelle’s brother happened to work for a talent agency and, well, the rest is history. If you feel like you have a story in you, then be disciplined and start writing it down.

Who knows, maybe Matthew McConaughey and Kate Hudson will turn it into box-office gold?

Grab your significant other or a gaggle of girlfriends, get some popcorn ready and a bottle or two of wine and enjoy a night with some of these films.

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