With Valentine’s Day on the horizon, the classic dinner-and-a-movie combo is the go-to date for couples everywhere. The Captain and I are making the same exact plan (with a few other flourishes), but it turns out that there isn’t really a good choice of romantic comedy out these days. The mid-90s to late 2000s blessed society with a plethora of romantic comedy choices, and I honestly miss those days when a new date movie came out almost every month. So, filled with nostalgia, I’ve compiled a list of my favorite romantic comedies.
10. Last Holiday. While I would count this as more of a Christmas holiday movie than a Valentine’s Day one, I still love this movie and its message. I’ll admit that most of its focus is on Georgia and her growth as a character instead of on the romance, but the beginning crush to eventual relationship between Georgia and Sean works nicely. It’s also great to see a male love interest who 100% supports the female lead and her goals and dreams. If it’s cold on Valentine’s Day, warm up with this romantic movie.
9. It’s Complicated. When you put Alec Baldwin, Meryl Streep, and Steve Martin in a romantic comedy together magic happens. Since it’s also a Nancy Meyers’ film its visually gorgeous, all of the food looks delicious, and the score is decadent. I love seeing a romantic comedy with an older female lead as opposed to the twenty-something, almost-thirty we usually get. There are plenty of laughs and a riotous scene involving marijuana, but also a lot of heart and sweet moments. Is it a love triangle at times? Yes, but it’s one that works. If you’re looking for some great actors in a hilarious predicament then pick up a copy of It’s Complicated.
8. My Big Fat Greek Wedding. I may not be Greek, but this movie about an overbearing family getting too involved with a relationship speaks to me (and my numerous cousins). The dating between Toula and Ian is realistic, and this feels like a natural relationship that would develop and become something over time. I think the wedding planning and ongoing cultural awakenings between the couple make for some good laughs and plenty of “aww” moments. I’d recommend this for a couple who come from different cultural backgrounds and can laugh about their crazy families.
7. Step Up. In addition to the film magic between Tyler and Nora, audiences get to witness the real world romance between Channing Tatum and Jenna Dewan. While it’s more of a romance than romantic-comedy, there are still good moments of humor. And the dancing is top notch! There’s so much sexual chemistry between Tyler and Nora, the soundtrack is amazing, and there are plenty of amazing scenes that you’ll remember long after the movie is over.
6. Just Like Heaven. While Sweet Home Alabama was a close contender, I think that the story and growing romance between Elizabeth and David is stronger. It’s a ghost-romantic-comedy without being too heavy or awkward in regards to that romantic obstacle. Reese Witherspoon and Mark Ruffalo are fantastic together, and I think that David makes for one of the better leads in these movies. More often than not, romantic comedies give more development to the female lead than the male but here they feel equally balanced. It’s a slice of heaven for a romantic night.
5. How to Lose a Guy in 10 Days. A movie with a title like that doesn’t sound romantic, but—trust me—there’s plenty of fun to be had in this romp. Andy is a columnist at a girly magazine tasked with writing an article on all the ways women scare men away; Ben is an ad man who’s betting that he can make any woman fall in love with him in order to land an account. Comedy ensues. This is one of those “high stakes” two-sides-of-the-same-story type movies where you want both Andy and Ben to succeed and also get together, but you know that it’s not going to work out that way. Kudos to Kate Hudson and Matthew McConaughey for a funny, yet personal, movie that’s fit for those couples who butt heads at every turn, but still love each other all the same.
4. The Five Year Engagement. Okay, so no one else I know likes this movie—much less loves it—which is why this list is personal. There’s something about this long-ass up-and-down movie that I simply adore. I’m not sure if it’s Jason Segal’s charming demeanor, Emily Blunt’s relatable character, or Chris Pratt’s best friend routine. I frequently make jokes that The Captain and I are living this movie (almost engaged two years), which he doesn’t find funny but I do. Which, in a way, is this movie. It is funny and charming and realistic and has a ton of great characters, but it’s also long, slow at times, and could have been cut down some. Still, this is a movie for those long haul relationships that may not know quite where they’re going, but they’re still not ending anytime soon.
3. A Cinderella Story. Finally, a kid-friendly rom-com! As most of my devoted readers will know, I am a sucker for all things Cinderella. This classic Hillary Duff and Chad Michael Murray film is no exception. It was one of the first “modern” updates of the fairy tales—replacing the glass slipper with a cell phone—and the development of the relationship between Sam and her “Prince Charming” is one of its great selling points. There are some great characters to build the ensemble, a nice early-2000s soundtrack, and a fantastic rain kiss. If you’re home with the kids or want some innocent rom-com fun then this is the film for you.
2. Kate & Leopold. In my eyes, Meg Ryan can do no wrong. She was the queen of romantic comedies in the 1990s and early 2000s and this was one of her classic working woman meets love-of-her-life combos. Hugh Jackman plays Leopold, a 19th century New York blue blood who accidentally follows Kate’s ex-boyfriend forward through time. There’s a lot of standard man-out-of-his-time humor, but also some good commentary on chivalry, manners, and dating in a Feminist society where women are expected to be driven and independent, but also want some of those classic romance moves that are in all the movies. If you’re looking for the movie that made butter sexy then put this on and enjoy the show.
1. You’ve Got Mail. I admit that I have a bit of a Meg Ryan movie collection, and this is my favorite of the bunch. While I also love the other Meg Ryan/Tom Hanks’ films, Sleepless in Seattle and Joe Versus the Volcano, this one is my favorite for one simple reason—books. Yes, it’s a little bit endearingly outdated in terms of Internet, but I like that. Kathleen is the owner of an independent bookstore; Joe is a part of the family that owns a mega-bookstore chain. They meet anonymously through a chatroom (remember when people did that?) and talk without knowing exactly who the other person is. At the same time, Kathleen and Joe meet in person as enemies for local bookstore territory in New York. There’s something about You’ve Got Mail that reminds me of simpler times when independent bookstores were easier to find, when the Internet was a little smaller, and when it was possible to find love in the unlikeliest of places. Put this movie in and you’ve got romance.