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My Top 10 Favorite Rom-Coms That I’ll Be Rewatching This Valentine’s Day

There is a 99% chance that I will be spending this Valentine’s Day watching my favorite romantic comedies. It was nearly impossible to narrow down all the funny and heart-wrenching rom-coms I’ve seen into a list of my top 10 favorites, but I did it! And you’ll definitely be able to tell which rom-com actors and actresses I love the most when they pop up more than once on my list.

#10: “Valentine’s Day”

This was obviously going to be on the list. I don’t know about you, but I LOVE a good star-studded ensemble cast. Something about the way that all the different stories tie in together at the end leaves me feeling very happy that everything worked out just right. Plus, Ashton Kutcher is very *chef’s kiss* in this movie. However, I’m going to assume that everyone expected this movie to be on this list, so that’s why I’m sticking it at #10.

#9: “About Time”

I feel like this one is a little more along the lines of a romantic drama with a bit of comedy here and there, but it’s a wonderful movie nonetheless. Can someone tell me how Rachel McAdams pulls off so many different types of characters? This rom-com definitely has a little bit of a twist that we don’t see in your typical meet-cute movie, and I think it is refreshing to see in all these movies depicting two strangers falling in love in New York.

#8: “Crazy, Stupid Love”

THIS MOVIE! I’m a huge fan of the Emma Stone and Ryan Gosling combination, and if you are too, you need to watch this movie (and “La La Land”). “Crazy, Stupid Love” encompasses romance mixed with comedy, making you laugh while you’re watching an eighth-grader fall in love for the first time or a law student venture away from what she’s used to romantically. This movie is one for the folks who love to laugh.

#7: “Fever Pitch”

My queen, Drew Barrymore, finally makes her debut appearance on my list as a beautiful businesswoman who starts dating a hot, young, Red Sox-obsessed teacher, played by Jimmy Fallon (who is fine AF in this movie). This particular rom-com does a good job of describing the relationship between two people who are attracted to each other but do not share the same hobbies or interests. It’s so cute and quirky, and I would place this closer to the #1 spot if #1 through #6 weren’t so amazing!

#6: “Made of Honor”

I think this romantic comedy was the first one I have ever seen, so it holds a special place in my heart. The classic realizing-you’re-in-love-with-your-best-friend trope is such a good one, and “Made of Honor” exemplifies it. Patrick Dempsey is the sexy best guy friend we all need in our lives, and watching him go from playboy to most iconic “maid” of honor ever is hilarious and endearing.  

#5: “Bride Wars”
My sister would have placed this movie at #1. Anne Hathaway and Kate Hudson are beyond funny as a pair of best friends, and the male leads (Steve Howey, Bryan Greenberg, etc.) are easy on the eyes. I also love the soundtrack to this movie, with “I’m Scared” by Duffy being my most played song of 2021 (LOL). This rom-com leaves us with the reminder that sisters always come before misters!

#4: “10 Things I Hate About You”

Ugh, talk about a classic! From Kat Stratford’s bad b*tch attitude to the visually appealing Heath Ledger starring as Patrick Verona and everything in between, “10 Things I Hate About You” follows the romantic lives of four high schoolers played by the most beautiful cast ever: Julia Stiles, Heath Ledger, Larisa Oleynik, and Joseph Gordon-Levitt. This rom-com combines the hilarity and awkwardness of high school with the reality of what it’s like to fall in love with the underdog.

#3: “The Proposal”

“The Proposal” rings in at #3 on this list due to its shock factor. Plot twists are thrown at you from all directions and I love watching Sandra Bullock and Ryan Reynolds in their respective roles in this movie. Our girl Betty White (may she rest in peace) kills it as Ryan Reynolds’ character’s grandma and is truly the glue that holds this movie together. This rom-com is useful for a good laugh or cry!

#2: “The Wedding Singer”
My rom-com king, Adam Sandler, makes his debut appearance on my list and Drew Barrymore returns for her second feature! “The Wedding Singer” is the epitome of 80s romance, hairstyles and all. Also, ironically enough, I’ve been listening to Billy Idol a lot lately, and he makes a hilarious cameo in this movie. I really do think Adam Sandler and Drew Barrymore are married in another universe because they just have so much chemistry and I love watching them in movies together! Plus, watching any movie featuring Adam Sandler will stock you up with witty one-liners for life.

#1: “50 First Dates”
Drumroll, please! “50 First Dates” is my all-time favorite romantic comedy. Drew Barrymore and Adam Sandler, the royalty of my romantic comedy hierarchy, appear yet again and make me fall in love with this movie every time I watch it. There is something so charming and unconventional about the plot of this movie, and it’s also the only other rom-com from which I definitely recommend the soundtrack. I’ll rewatch this movie any time of the year just to get that warm feeling inside from watching the grand romantic gestures performed in this movie.

This list was almost impossible to compile, but I hope you enjoy it! Valentine’s Day isn’t just about going out with a significant other, it’s also about loving yourself and doing things that make you happy. If that looks like staying home and watching the greatest romantic comedies of all time (IMO), then this is the list for you!

Anna Simoes

CU Boulder '23

Anna is a junior at CU as a Speech, Language, and Hearing Sciences major along with a Spanish minor. She is from the Bay Area in California and loves to attend concerts and go to the beach in her free time! When it's snowy in CO, she spends time with her cat, Ren. :)
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