My Top 5 Hopeless Romantic Guilty Pleasures

There are hopeless romantic movies that I love that I wouldn’t consider guilty pleasures. In a way, it’s probably my favorite genre– if you can even call it a genre, the “hopeless romantic” genre–  and I don’t feel guilty about that in the slightest. One of my favorite movies of all time is The Apartment. The Apartment is hopeless romantic to its core — but in a healthy way.


What do I mean by that? Well, I view The Graduate as hopeless romantic in an unhealthy way. You know that scene in (500) Days of Summer, when they show young Joseph Gordon-Levitt’s character misreading The Graduate and thinking it’s about true love? And as a result, it landed him in in a lot of trouble, love-wise? I fell for the same trap. I first saw it when I was 16 and in my eyes, Ben’s trek up to Berkeley to profess his love to Elaine was what romance was all about. And admittedly, on repeat viewings, I still felt this way. Until recently. About a year ago, I finally began to realize just how creepy it all is. Suddenly, Ben’s “romantic” adventure to Berkeley was stalker-ish. And his crashing of Elaine’s wedding was no longer seen as, “Yeah, you go, Ben!” No, I now saw it as, “Dude, you gotta give it up. For your own sake. This is taking it a little too far, no?” It all seemed ridiculous — even on Elaine’s part. When she visits him in the room he’s renting out in Berkeley and they talk about love, you can’t help but wonder if this is supposed to be serious. Sure, they’re young, college-aged, and horny. But we’ve all been there — the thing is, I never would have crashed a wedding or asked a girl with whom I only went on one date to marry me, no matter how young and horny. Or, maybe I did it in my own, modern way, by jumping into a long-term relationship with a college girlfriend despite my impending graduation, without really thinking it through? Is that similar, in a way?


Regardless, this is why I see The Graduate as an unhealthy hopeless romantic movie. It feeds the worst impulses of a hopeless romantic. And this isn’t to denigrate the movie as a movie. No, the thing is still a goddamn masterpiece, technically and structurally speaking. And there’s no debating the hold it has had on the cultural zeitgeist for fifty(!) years. But, from a personal standpoint, as a hopeless romantic who needs all the help he can get to not make the same mistakes in love, I needed to break away from this movie. I needed an intervention.

I took it off the top of my list of Favorite Movies and replaced it with The Apartment (which was already in the Top Five). The Apartment is healthy hopeless romantic because the C.C. Baxter character pines but doesn’t make it all about him. It’s unrequited love but unrequited love handled with class. He doesn’t make the woman who doesn’t feel the same way the enemy, as some men do. He feels sad about it, but that doesn’t turn him into a dick. He’s an example to follow for all hopeless romantics.

What I did with The Graduate is something I’ve done with other movies as well — I have at times lived my life through them, and hopeless romantically, that’s not the best idea. What were those movies? Below are five, ranging from movies of my youth, to more recent fare.



Of course, Titanic, right? Titanic and I have a special connection. That sounds weird, but we do. I saw it when I was seven years old and immediately after, asked the hairdresser to “cut my hair like Leonardo DiCaprio’s in Titanic.” See? Special connection. Seven is relatively young to see this movie for the first time, I’ll admit. And that’s probably why it had such an effect on me.

There were two things about DiCaprio’s Jack Dawson that really spoke to me. The poor guy going after the rich girl dynamic and his drawing skills. I was like, yeah, that’s me. I was lower middle class and I drew (cartoons mostly — not naked French women, but still…). Never mind that he’s a character without flaws and therefore kind of boring — do you think that shit really mattered to me at seven? Character development? What’s that?

It was Jack Dawson that started it all; I am a hopeless romantic because of him. I have a tendency (one that I’m trying to kick) to live my life like a movie, forcing grand romantic gestures instead of just letting things be or just happen, because of this character. And I hate him for it.

The Notebook


Here’s another poor guy gets the rich girl scenario (I know it’s hardly an uncommon trope). Interesting to remember this movie in context — this was 2004, before peak “hey, girl” Ryan Gosling. Rachel McAdams, coming off of Mean Girls, was arguably the bigger name attached to this, but still, relatively unknown. It helped the movie kind of come out of nowhere.

And say what you will for the movie as a whole, but it’s hard to deny that these two had chemistry (despite reports that they hated each other on set — which they apparently got over as they dated for a while, didn’t they? Anyway…). I was in middle school when it came out and fell in love with Rachel McAdams and fell in love with the idea of growing a grizzly-man beard while restoring an old house.

About Time


Another McAdams movie, but I think a better one than The Notebook, though I can admit About Time has some flaws. Particularly, the whole time travel thing wasn’t as well thought out as it should be. There are stretches that don’t make much sense. This seems like a pretty big deal in a movie kinda-sorta about time travel. But it’s not — at least I don’t believe it is. There’s a warmness to this movie, especially in its portrayal of families that you can’t resist, and that’s what matters. That’s the point of it all.

It’s also about love, naturally, and it’s kind of comforting to watch this relationship begin and grow into something deeper. Yes, there’s the typical Richard Curtis over-sentimentality, but in spite of that, there’s a natural feel to this movie and to McAdams and Domhnall Gleeson’s characters’ love. I look at this as a New Years’ Eve movie– like The Apartment and When Harry Met Sally, not just because of its opening scene taking place on New Years’ Eve, but because there’s an optimism to this movie that I find occasionally necessary. Especially these days.

Love Actually


Okay, another Richard Curtis. (Does this make me a bad movie watcher? Is it bad that I fall for Richard Curtis’s shit so easily? Whatever.) Love it or hate it, Love Actually is a huge thing. And I’m on the love it side. Perhaps it’s because it’s been ingrained as tradition in my life for so long now that I just view it as something like It’s A Wonderful Life. And no, I’m not comparing the two filmmaking-wise. But I mean, you know, as a holiday staple. (For the record, I consider It’s A Wonderful Life a hopeless romantic movie — but one that I’m not guilty about. This list is guilty pleasures.)

Anyway, back to Love Actually. This Guardian piece by Hadley Freeman is very interesting and, when I read it a few months ago, made me think of this movie in a different light. However, it still remains on my list. Maybe I’m a sucker, quick to embrace the feel-good, but if there’s one thing I’d say about that Guardian piece, is it takes the movie too seriously. The ridiculousness and cringe-worthiness and roll-you-eyes-at scenes — that’s what makes the movie enjoyable for me! But maybe I’m wrong. Because, yes, there’s some concerning stalking and office harassment going on in this and I’m not condoning that. In fact, it’s important that the Guardian piece points all of that out — and maybe that’s why I’ll just watch the Bill Nighy, Martin Freeman, and Liam Neeson/stepson scenes in the future, skipping the rest of it. Worth a shot.

10 Things I Hate About You


Full disclosure: I’m not really that guilty about liking this. I actually think this is a masterpiece of the teen-comedy genre. But I’m including it on here nevertheless because what the hell. It’s not a movie I’d put on my Top Ten list or anything. But talk about a movie inspiring a hopeless romantic… Heath Ledger’s “Can’t Take My Eyes Off Of You” serenade on the bleachers is just asking to be imitated (poorly) by hopeless romantics everywhere.

Joseph Gordon-Levitt’s character is a stand in for all love struck high schoolers– and all hopeless romantics. It’s great to be able to relate to someone in your pathetic-ness. But a sweet pathetic, you know? (Or at least you hope.) But this is really about Julia Stiles and Heath Ledger. They nail it. And they prove (or their characters do at least) that even those who scoff at love or treat it like a game can fall. Love can conquer anybody. And that’s just what a hopeless romantic wants to hear.


3 thoughts on “My Top 5 Hopeless Romantic Guilty Pleasures

  1. What a fantastic list, I feel I could have put it together myself! I am so beyond happy that you included About Time, I totally love that film so so much. I am pleased to find someone else who loves it too!

    Liked by 1 person

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