The Most Romantic '90s Movies To Watch On V-Day

by Mary Grace Garis
20th Century Fox

It's OK to admit that you're going to have one of those low-key Valentine's Days with endless Chardonnay, enough junk food to make a Gilmore girl blush, and the romantic comedy of your choosing. I mean, if you're going to be reminded that you're single as hell, it might as well be with something entertaining, instead of your cousin's 400 Instagrams of the bouquet she received at work. Of course, it goes without saying that these are dark times we live in. So, why not spend the holiday with the era you love most... the '90s? For your Valentine's amusement, I rounded up a collection of some of the best romantic films from the '90s — and yes, that's considering whatever your idea of romance is.

Perhaps you love retreating into teen movie remakes of classic literature. Or what if you want to follow a geeky journalist as she hunts out a big story... and potentially love? It could be possible that you feel like watching two soulmates connect over the internet and clash in real life, before Tinder made that the status quo.

Or hell, maybe you just want to drool over Leonardo DiCaprio. Whatever the case, I have you covered. Scroll down for proof.


'Pretty Woman'

In which rom-com queen Julia Roberts plays a hooker with a heart of gold and manages to snag a happy ending for herself.

Stream here.


'While You Were Sleeping'

That awkward moment when you end up involved with your comatose fake-fiancé's brother. Don't worry, it all works itself out in the end.

Stream here.


'Never Been Kissed'

Twenty-five-year-old journalist Josie goes undercover for a high school exposé and ends up smitten with her English teacher. Girl, I can't blame you.

Stream here.



Oh, come on. You haven't been able to escape Titanic over the past two decades, and there's a legitimate reason behind that. No matter how many people have parodied that "Jack, I'm flying!" scene, it's still an epic, enduring romance. Get two bottles of Barefoot and settle in.

Stream here.


'You've Got Mail'

Even badly dated Nora Ephron is better than no Nora Ephron. And although this one definitely shows its age as an AOL-era love story, I still tear up when Joe Fox asks for Kathleen Kelly's forgiveness... even if he doesn't deserve it.

Stream here.



Our modern Emma Woodhouse tries her damnedest to play cupid, with interesting results. We all know and love the story, and it's always worth rewatching, if only to appreciate the dreaminess of a young Paul Rudd (who, weirdly enough, looks a lot like old Paul Rudd).

Stream here.


'My Best Friend's Wedding'

In which rom-com queen Roberts plays a resturaunt critic trying to win over her best friend before he gets married to someone else.

Stream here.


'Shakespeare In Love'

Anything involving William Shakespeare, even a fictionalized love affair, has got to be wildly romantic, right? Speaking of which...

Stream here.


'Romeo + Juliet'

Baz Luhrmann does love and anachronisms right here (can't say the same for The Great Gatsby), and seriously, how can you deny the youthful beauty of Leo. And also...

Stream here.


'10 Things I Hate About You'

This one's got Heath Ledger (R.I.P.), a tiny Joseph Gordon-Levitt, and David Krumholtz, if you're into that kind of thing (which I am). But most importantly, it's anchored by Julia Stiles as fierce riot grrrl Kat Stratford, so you don't have to worry about your feminist cred diving in.

Stream here.


'The Wedding Singer'

It's one of the few still-solid Adam Sandler flicks, it's hilarious for its '90s view of '80s nostalgia, and it's also very, very sweet.

Stream here.


'Cruel Intentions'

This is if you're craving a sexier Valentine's Day versus a romantic one. No matter what kind of last minute declarations Sebastian makes, he still rings as a sociopath to me. An incredibly hot sociopath, but a sociopath nonetheless.

Stream here.


'Reality Bites'

Oh, Lelaina, I know you're trying to just figure it out, but you don't have to entertain a love triangle with a well-adjusted corporate drone and the very definition of slack. But hey, as an ambitious musician-obsessed girl, I get it.

Stream here.


'Notting Hill'

In which rom-com queen Roberts plays a Hollywood actor who falls for a handsome bookstore owner. Man, that smile is everywhere.

Stream here.


'Before Sunrise'

If you feel like spending the night with two souls just passing through Vienna, consider taking a trip with these two.

Stream here.