I love movies. I don't tend to categorize them into good and bad or by genre or period or country of origin. There are just the ones I really like, which is a lot of them, and the ones I don't, also a lot of them. I can tell the difference between quality and mediocre acting, direction, dialogue, production, etc. And I can discuss all that with you during my bruschetta and your risotto or whatever. But I am just as happy talking about the corner of a man's mouth or the way a couple's hands first meet and etcetera.
I read some Valentine’s Day movie lists recently, and about the only thing we all agreed on was 10 Things I Hate About You. So I started writing some down, and wow, is that hard to do. I’m sure this list isn’t even personally comprehensive, but I wouldn’t know how to make it so without way more effort than I am willing to put into it. The name links are to places you can watch them for free (if they're underlined, they'll auto-play,) or at Netflix or for 3-4 dollars at Amazon, and the other links are to various articles about them.
Looking it over, some obvious double features come to mind. I’d happily pair 10 Things with Drive Me Crazy. Make no mistake; the latter is not as good a movie as the former. Yet it’s easy to watch, endearing, and there’s plenty to both aw about and guffaw about. You can admit to enjoying it while making fun of it. Both these movies were released in 1999, which was kind of the apex in teenage transformation romantic comedies. And maybe Adrian Grenier was no Heath Ledger, but you would still want to ruffle his hair if you were standing near him, and he would be good to kiss (and something more, apparently, according to this sort of meta-trash article.)
I’d pair Moonstruck with Wild At Heart for an intense Nicolas Cage double feature, which is a sentence I could never have imagined writing before I just did. These movies are not alike. They just both have Nicolas Cage in them, and are from the same time period, and I think you could get down a sizeable volume of wine during your viewing of them. I’m not sure which I’d say to watch first; kind of depends on how you personally see life playing out. Best not to read too much about the latter before watching, just know it’s a little sexy, a little violent, a little gross, and also kinda sweet. You know, David Lynch. Not everyone would find Wild At Heart romantic, though, plus you have to buy it or watch carefully, so you could always watch Moonstruck with Big Night, which is a wonderful romance with food.
My favorite light romance of all just might be A Little Romance. (But it might not be; I don’t do favorites very well.) It’s both dreamy and cheesy, and if you have a soul, you won’t care about the cheesy parts. Or that you would be watching it for free since it's 38 years old and...worth it. Its most obvious double feature partner on this list is Moonrise Kingdom, but I know some people have a deeply inexplicable dislike for Wes Anderson films, so if that’s you, god help you, watch it with Roman Holiday, instead.
For pure romance, I love Portrait of Jennie. For an intense double feature, follow it up with Love is a Many-Splendored Thing. I’m not a great fan of Jennifer Jones, but I appreciate her in these films, and a couple others. You could instead have a Jennifer Jones double feature which also features Joseph Cotten by pairing it with Love Letters, which is uneven, but ends satisfactorily. (Jones and Cotten were in four films together, and my favorite is actually Since You Went Away, only it is not a Valentine’s Day type of movie.) Or you could pair Portrait of Jennie with a Joseph Cotten/someone else film: September Affair if you lean bitter, I'll Be Seeing You if you lean hopeful.
For a long evening of beautiful what ifs: In the Mood For Love (Korean) and The Remains of the Day. And Romantics Anonymous (French) and Monsoon Wedding (Indian) are probably best on their own, but would be fun together, or you could watch either one of them with Shakespeare in Love.
Finally, for reasons I cannot begin to explain, I have watched What A Girl Wants so often I could recite its dialogue. It’s romantic mostly if you want it to be. It’s the B side of A Little Romance, I think, but it would be more fun with Sweet Home Alabama for a light-hearted look at 15 years ago, or with Say Anything for a more direct parallel and so that you can say you know what a good teen romantic comedy should look like. Or you could follow it up with A Single Man for a reminder of how good Colin Firth can be with great material, but there is no other common factor involved.
It took me awhile to decide whether all the title links should go to descriptions/reviews or places to watch, but I went with the latter because it felt most useful. After all, you can just go to IMDb and plug in all the names you want to see, like this.