Valentine’s Day Special: Ten Favorite Romantic Movies

Welcome to Love Week at All Eyes on Screen! Each day I’ll have a post about something that I love. Valentine’s Day is here, so I’ll be listing off my top ten favorite romantic movies that I love.

But first, I must ask, Why are they called “romantic comedies”?  Many of them are not funny, and there’s certainly plenty of comedies that are low on the romance.

Wikipedia defines a romantic comedy as the following:

a film that includes “light-hearted, humorous plotlines, centered on romantic ideals such as that true love is able to surmount most obstacles.”

Even as a chick, that definition rubs me the wrong way. There’s something annoying about the idea that everything can go wrong, but “true love” will make it all go away. It’s not that I don’t believe in true love or its power to overcome difficult times. But it seems to painted in such a pretty way that we always see that physical infatuation, that two-month period in the relationship filled with butterflies and roses. Great film rides off drama. Drama’s a natural ingredient that must be placed in film in order get the protagonist from point A to point B. And such is the job of all storytelling, regardless of the format or channel.

Perhaps the genre “romantic comedy” receives the great beating in film today. Maybe it’s the lack of good drama that drags it down. We have all of these unrealistic situations occurring, such as the film Life as We Know It (2010). Really? A romantic plot born from a couple dying and willing the care of their child to two complete strangers who dislike each other? (Sorry – I’m not much of a Katherine Heigl fan, all.)

Yes, some romantic films work well in a more dreamy-like state, such as 13 Going on 30. But perhaps that success lies in that the movie doesn’t attempt to take itself seriously like Life as We Know It. Romantic films like My Best Friend’s Wedding set the bar for more realistic romantic flicks. Or maybe the idea of an ending that didn’t end happily became more accepted because we deem happy endings as unrealistic.

Regardless, there’s not a more popular genre to receive low scores from critics than romantic comedies. Speaking for myself, I don’t care to watch romantic films for their critical acclaim; I’ll admit wholeheartedly that I watch them for that feel-good feeling, even if they have (multiple) fluff moments.

Honorable Mention: A Walk to Remember (2002)

This movie almost made my top 1o list. Mandy Moore and Shane West are probably each credited most for this film. Neither have made as successful films since, although West stepped it up when he joined the main cast of the TV show remake, Nikita. Moore also has upcoming television plans. Regardless, this film is typical Nicholas Sparks crap. And I enjoyed it. It’s almost painful to admit since I abhor Nicholas Sparks’s obsession with pairing characters together and then ripping them apart for unrequited love, death, mean relatives, war, the list goes on and on. I did love Mandy Moore in this film, though. She has a great singing voice and gets to showcase some of her vocal talents on screen as well as on the soundtrack.

10. The Wedding Singer (1998)

The Wedding Singer is one of my favorite Adam Sandler films. He’s absolutely hilarious, especially in some of his older movies like The Longest Yard (2005), Mr. Deeds (2002), and Happy Gilmore (1996), but I think he hits his stride in this film. He helms this obnoxious humor while still earning some sympathy from viewers. He and Drew Barrymore work great against one another, although I much prefer The Wedding Singer over their second attempt 50 First Dates (2004). This scene is one of my favorites; the Billy Idol character really adds to the humor of it all.

9. The Wedding Date (2005)

The majority of critiques on The Wedding Date is negative. I know, I know. I would call The Wedding Date a guilty pleasure, but I guess it doesn’t add up much to the idea of “guilty pleasure” when people are calling Jersey Shore and all shows Kardashian “guilty pleasures.” Why do I like this film? It’s hard to say. I guess I just love Debra Messing and Dermot Mulroney together in it. I like that it takes place in London, and I love the score by Blake Neely. Not to mention, Michael Buble and Maroon 5 make up much of the film’s soundtrack. If you’re a fan of this movie, you might want to check out the new TV show Smash, starring both of The Wedding Date‘s Debra Messing and Jack Davenport.

8. How to Lose a Guy in 10 Days (2003)

Kate Hudson is hysterical in How to Lose a Guy in 10 Days. Kate Hudson and Matthew McConaughey are another one of those duos that play great against one another, although their second attempt Fool’s Gold (2008), fades in comparison. Hudson puts McConaughey through hell, and it’s only fitting for us to watch him suffer. The video is one of the funniest scenes in the film.

“You killed our love fern!”

7. (500) Days of Summer (2009)

Many people do not consider (500) Days of Summer to be romantic, but it just happens to be one of my favorite romantic movies. Yes, I know it follows the same pattern as My Best Friend’s Wedding, which I’ll get to soon. But Marc Webb’s creation is wholly original and altogether enjoyable and romantic in many scenes. I love his storytelling method in the film, and one of my favorite scenes is of Zooey Deschanel and Joseph Gordon-Levitt walking through IKEA, as well as the dance sequence to the tune of Hall and Oates I included. The scene I’m most moved by though is one of the scenes near the end, when Gordon-Levitt gives a little speech about love in the middle of a work meeting. He’s clearly lovesick and brings a hint of irony about how as greeting card writers, they tell people’s loved ones that they love them for them. And what is the specialty in that when you can tell a person yourself how you feel?

6.  My Best Friend’s Wedding (1997)

The first time I saw My Best Friend’s Wedding, I had no idea that Julia Roberts and Dermot Mulroney would not end up together. In fact, I was stunned to see Cameron Diaz whisk Mulroney away at the end. I love the idea that two people, who happen to be best friends, made plans to someday marry if they never found another person. And then off goes Mulroney and finds the youngest, most naive girl to fill the shows Roberts decided that she should have filled instead. She hatches a plan to steal the soon-to-be groom, and it makes sense. They have this brilliant chemistry, and of course they ought to end up together. But they don’t; such is life. The end leaves a bittersweet taste in your mouth, because the fight is finally over, despite her losing it. I love the use of Union Station and the old Comiskey Park (home of the White Sox, yo!)  in this film. It’s nice to see some Chicago scenery be taken advantage of! Check out the video for what I think is one of the best scenes in a romantic movie.

5. It’s Complicated (2009)

On Christmas Day in 2009, a few friends and I planned to see the first Guy Ritchie Sherlock Holmes. We were pumped until we found out that it was sold out and that we had to settle for It’s Complicated, the rom com starring Meryl Streep, Steve Martin, and Alec Baldwin. The unfortunate affair turned out to be a fantastic film after all. It’s Complicated is proof that Meryl Streep is capable of playing normal, every day people. There are so many hilarious scenes in this film, that it’s one of the few rightly dubbed “romantic comedy.” From Steve Martin and his divorce tapes, to John Krasinski playing the lovable son-in-law, It’s Complicated has become one of my favorite go-to romantic movies.

4. You’ve Got Mail (1998)

You’ve God Mail is a classic romantic movie in most people’s books, and it’s definitely one in mine. It’s one of three films that Tom Hanks and Meg Ryan star in together, and they do so with a perfect connection. It brings me back to the time when AOL was the big thing around the Internet, and we had to listen and wait for the dial connection before we could use AIM or send an email. It’s the recycled story of two people who hate each other, and later learn to like one another as they start to learn and understand more. Meg Ryan has done her share of these films, and Hanks really isn’t a stranger to the genre either. The end scene is pitch perfect. Enjoy it!

3. Notting Hill (1999)

Notting Hill is another romantic movie with Julia Roberts that I love, and my first one including Hugh Grant that makes the list. I really like both in the genre, although I’m of the belief that both made their best romantic films in the 90s or early 2000s as opposed to more recent times. I love this film. It’s completely a dream gone reality, bringing everyman Hugh Grant into the movie star sphere of Julia Roberts, where an unlikely connection is formed. She experiences time around his humble friends and family, while he starts to wonder if she’s stringing him along or truly into him. She brings her world into his when she says the famous line, “I’m also just a girl, standing in front of a boy, asking him to love her.”

2. 13 Going on 30 (2004)

Jennifer Garner seems to be more accepted acting in rom coms these days, and one of her best ones I think is 13 Going on 30. She bears all the youthful innocence necessary for her character, and the very underrated Mark Ruffalo does a nice job playing opposite her. It’s also pretty hilarious to watch Andy Serkis actually play a human on screen, much less his giddy character in this movie. The film does a nice job of putting life in perspective. Although must of us probably won’t have our futures defined by the friends we had in high school, we will have memories of that time that will stay long with us. It also does a nice job of showing us that who we pick as friends often influences our behavior and changes us in the future. Overall, 13 Going on 30 fits the description of being light-hearted and sweet. Oh well.

1. Never Been Kissed (1999)

Never Been Kissed is my favorite romantic movie. It’s about a dork who returns to high school on an undercover assignment to find out about today’s teenagers. Drew Barrymore blossoms at this geeky character who desperately seeks to fit in. I haven’t seen another movie similar enough that showcases a character quite like the one Barrymore creates in Never Been Kissed. My favorite scene is when she tells her story via voice over. It’s a great way to wrap up the film. I included the final scene of the film because it’s all I could find on YouTube. It’s also one of my favorite film kisses.

OK, your turnWhat is your favorite romantic movie? Or what is one of your favorite scenes from a romantic movie? Don’t be shy . . . 

35 thoughts on “Valentine’s Day Special: Ten Favorite Romantic Movies

  1. You’ve already mentioned my modern favorite – (500) DAYS OF SUMMER – so beyond that, I give you another lucky seven…

    SAY ANYTHING (How did *that* miss your list??)


    • Haha, thanks so much for sharing yours, Ryan! Yes, (500) Days of Summer is brilliant. Absolutely love that film.

      I LOVE When Harry Met Sally, but no, sadly it did not make my FAVORITES list. I also really enjoyed CSL and Sleepless in Seattle. I’ve never see The Apartment or It Happens One Night. I’ll have to check those out.

      I actually didn’t care for Love, Actually at all. There were parts I didn’t mind, but overall, I didn’t care for the film. And as for Say Anything? Well, of course, I loved it! It’s a Cameron Crowe flick and I’m loyal to him, even if I don’t care for some of his other films (read: Almost Famous, We Bought a Zoo). Loved Say Anything, but it didn’t make my top 10 favorites.


    • I definitely understand. Typically not my favorite films–and definitely not genre–in any sense, but fun to think about around this time of year. Yes, I think The Wedding Singer is one of his best films. The Waterboy is funny, too, although I haven’t seen it from start to finish. Sandler’s a crazy one. Thanks for reading!


  2. 13 Going on 30 is such a guilty pleasure for me. I don;t find it particularly great but there is something about that movie that keeps me coming back. Probably seen it 20 times by now, mostly when it’s on cable 😉


    • Haha, that’s interesting to hear. Yeah, I don’t know what it is about that film, but Jennifer Garner and Mark Ruffalo are great in it together. I think it’s that whole idea of being kids in adult bodies that gets it for me. I love how she reacts to the change, and I don’t think many other actresses could pull it off quite like Garner did.


      • All I know is that every time I think of the movie, Michelle Branch’s song “Why Can’t I” pops into my head, and I see Jennifer Garner hailing a cab to track down Mark Ruffalo before he gets married.


  3. Yay for 500 Days of Summer. I haven’t seen a lot of these as I’m generally not a fan of romantic comedies. I think the reason they get panned so much is because of their formulaic stories. You can watch the trailer for most of them and know exactly how they will end. I hate seeing a trailer where the boy and the girl meet and hate each other and the first half of the trailer is quite funny and then suddenly the music changes to something really soppy and we start to see them pair warming to each other. But then again I watch slasher films so I can’t really complain about stories all being the same. I’d also have ‘Four weddings and a funeral’ over ‘Notting Hill’.


    • Haha, yeah, that seems to be a favorite on the list, especially among the guys. Haha, very understandable. I would agree that most of them are like that, although I think both (500) Days of Summer and My Best Friend’s Weddings are exceptions to that rule. I try to stay away from romantic comedies like “Leap Year” and others that completely reveal themselves in the trailers as much as possible so as to not waste my time.

      Haha, I love your description of most rom com trailers, and I can definitely see where you’re coming from. It’s an overused concept that’s rarely executed well enough for any of us to appreciate. I’ve heard people heap praises onto Four Weddings and a Funeral, but I’ve never actually watched it from beginning to end.

      Everyone has their genre they like more than others, and while it’s definitely not romantic comedies for me, there are still quite a few good ones out there, or at least some function as guilty pleasures for me 🙂


  4. Love your breakdown of the “romantic comedy” term. I feel like the best rom-coms either go all in on that, as you say, dream-like state, like “Love Actually” which I absolutely adore, or they skillfully blend the realism and the romance (and that ain’t easy), like “Annie Hall”, which as far as I’m concerned is the be-all, end-all of the genre.


    • Thanks, Nick! Ahh, so many people love “Love Actually,” but I guess I never “got” what was so great about it. There were parts of that film that I enjoyed, especially the story with Hugh Grant, but most of it just kinda fell by the wayside for me.

      OK, Annie Hall has just made it onto my need-to-see list. I keep hearing about how great that is, and with that kind of review from you, I’m going to have to check it out now. Thanks!


  5. Glad you’ve got (500) Days of Summer up there, I’d put it in there as a favourite romantic film of mine too.

    I have a soft spot for The Time Traveller’s Wife. It’s the cast I think, but that’s a good, romantic weepy I can get behind.

    Before Sunrise and Before Sunset – I would call them modern day romantic classics.


    • Yep! It was impossible to leave off my list. Simply one of my favorites.

      Haha – I enjoyed The Time Traveler’s Wife, but I don’t think I could watch it again. Almost too sad for me. Rachel McAdams and Eric Bana are great in it though!

      Haven’t seen either of those! I’m glad to get some feedback, because there’s so many good ones people have talked about here that I haven’t seen. Thanks for the recommendations!


  6. Great post, Kristin! You’re right that most rom-com are neither funny or deeply romantic, they’re faux romantic I’d say as a lot of people equate love with sex nowadays. That’s why I avoid movies like Friends With Benefit and the likes. I only like a few rom-coms, two of them are on this list: You’ve Got Mail and Notting Hill (I don’t think the K should be there :))

    My all time favorite that I did for V-day definitely has a perfect balance of romance AND comedy, hence it’s the quintessential rom-com and a timeless one at that.


    • Thanks, Ruth. Very true. For the most part, I true to avoid ones that stray from the idea, although sometimes I like watching them to get a grasp on what exactly Hollywood is defining “true love” is at the time. It’s rare to find a rom com that has great sense of intelligence, and sometimes I think you have to watch beyond the trailer to find it. Haha, thanks for that – I ALWAYS have in my head that a “K” should go there, and I’m not even sure why! Haha.

      Exactly. Well, after writing this post, I’ve got quite a few suggestions for some good rom coms, or so I’ve been told, so I look forward to hopefully seeing some movies that have that timeless quality. It’s certainly not my favorite genre of film by any means, but I enjoy taking a little time out of each year to appreciate the ones I do enjoy.


      • I think so too! Yeah, that scene does a great job of bringing a realistic mindset a lot of us hold to life.

        BTW, Xtian – do you have a site? You should link it so I can check it out if you do!


        • yea MIP was quite interesting…cool story…also a bonus cause i’m obsessed with rachel mcadams….and no mam i do not have a site…not really a big blogger…just like to throw in a comment here or there when i feel strongly towards something lol…

          p.s. another great movie to check out…Cherry


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