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Rom Com Recommendations

  • Writer: scarejonathan98
    scarejonathan98
  • Feb 14, 2024
  • 7 min read

Updated: Apr 28, 2025


With today being Valentine's Day, I thought it would be fun to share some romantic comedy recommendations. I am not a big fan of romantic movies and to a lesser extent, Rom-Coms but Sarah enjoys them quite a bit. Even though I am not a big fan, it has been fun to enjoy these with her. To give a broad range of films I tried to include Rom-Coms from multiple different decades from the 1980's to today. So here are some romantic comedy recommendations to watch this Valentine's Day. 


1980's

I. The Princess Bride

Kicking off the 1980s is The Princess Bride. This movie is probably the loosest definition of a rom-com but I still think it is considered one. This movie is just a lot of fun and manages to do a great job of balancing romance with fantasy and humor. This is just a great swashbuckling fantasy adventure film. There are so many memorable lines and scenes like "Hello, My name is Inigo Montoya, you killed my father. Prepare to die". All of the characters are just so memorable and fun with each character getting their own little moment to shine. There are so many silly stupid moments in this but also a lot of fun action scenes and some great romantic moments. The romance in the movie is also done very well. Westley and Buttercup are so great together. We get to see the lengths Westley goes to rescue her and end up with such a great resolution. Overall, this is a great movie with lots of romance, humor, and adventure. 


2. When Harry Met Sally

When Harry Met Sally is probably one of the greatest rom-coms of all time. If you look at lists online of the best rom-coms ever, pretty much all of them have this movie on it with many of them having it at number one. This is just a classic story while also not being a typical rom-com. Unlike most other rom-coms, the main characters don't fall in love or date right away. Instead, they grow as friends until the very end. Meg Ryan and Billy Crystal are great as the leads in this film and have great chemistry together. I really enjoyed the humor in this film. It isn't in-your-face humor but more subtle. It reminded me a lot of Seinfeld where the humor comes from characters just having casual conversations. I also like how the movie shows their relationship progressively builds until they grow to have feelings for each other. It is also different than most rom-coms as it takes place over years instead of just falling in love in like 5 minutes. I really enjoyed this movie and it is probably one of my favorites on this list. 


1990's

3. Sleepless in Seattle

Starting off the 1990's, we have Sleepless in Seattle. Sleepless in Seattle is the second movie on this list to star Meg Ryan. This is another classic of the genre and a movie almost everyone knows. This is a bit untraditional of a rom-com as the main couple don't actually meet until about the very end of the movie. I like that this movie talks about dealing with loss and getting back into the world after losing a spouse. The dynamic between Tom Hanks and his son is a lot of fun. Their relationship is the real focus of this movie. The story itself may be a little clunky and the ending may be a bit cheesy but overall it makes you feel good and works well as a rom-com. 



4. You've Got Mail

You've Got Mail is the second rom-com from the 90s to star Tom Hanks and Meg Ryan except this one takes place in New York City instead of Seattle. This is probably my favorite Rom Com. While the technology itself is pretty dated, I think the movie could easily work in today's world which makes it more relatable and interesting. Even the whole lot about a big corporation shutting down local shops is very prevalent today. I thought Tom Hanks and Meg Ryan were so much fun together. I also enjoyed the NYC setting. This is one of the quintessential rom-coms and is usually on everyone's list of the best or most iconic rom-coms. Sarah even enjoyed this movie after being skeptical at first because it is an "old movie". In the end, this is just a classic rom-com with an iconic couple. 


2000's

5. How to Lose a Guy in 10 Days

Kicking off the 2000's is How to Lose a Guy in 10 Days. This is a movie that really irritated me in parts but in this case, that is a good thing as it is the goal. Kate Hudson does a great job playing this girl trying to get a guy to break up with her and does all the wrong things that would always make a guy mad. Matthew McConaughey is also a lot of fun in this movie as he tries so hard to not get irritated and win Kate Hudson over. This movie has a lot of the classic rom-com cliches but does them well. I also thought the basic plot was super interesting as it was a bit different than the normal rom-com. Sarah also enjoyed this movie and thought it was funny how irritated I got with the Kate Hudson character. Overall, this was a very fun movie and another rom-com that I would probably re-watch. 


6. 50 First Dates

50 First Dates is one of the most surprising on this list as I am usually not a big fan of Adam Sandler. I'm not a huge fan of his style and sense of humor but I thoroughly enjoyed him in this movie. In this movie, Adam Sandler has the difficult task of having to win over a girl with short-term memory loss every day. I thought this movie was incredibly charming with a lot of funny and sweet moments. Adam Sandler and Drew Barrymore have great chemistry together and Drew Barrymore is great as this innocent woman without any short-term memories. I thought it was very creative how Adam Sandler managed to win Drew Barrymore over every single day. While it may raise questions about how the movie turns out in this end, I thought the ending was very sweet and satisfying. In the end, this is a sweet comedy with a performance from Adam Sandler that I actually enjoy. 


7. The Proposal

The Proposal is one of Sarah's favorite rom-coms and is Sarah's recommendation on this list. This movie follows Sandra Bullock and Ryan Reynolds as they put together a green card wedding so Sandra Bullock can still be in the USA. Both actors are always quite charming and in this movie manage to have great chemistry together. There are a lot of funny moments with Sandra Bullock meeting Ryan Reynolds's family and Sandra Bullock and Ryan Reynolds pretending to be engaged. I am not a huge fan of this movie but Sarah really enjoys it and finds it incredibly funny. Overall, while it is still at the bottom of my rom-com list, I enjoy watching it because Sarah enjoys it. 


2010's 

8. Crazy Rich Asians

Crazy Rich Asians is the 2010's representation on this list. This is another of Sarah's favorites but is one I like considerably more than The Proposal. It has so many moments that make her laugh out loud. She also really enjoys the characters and romance. I enjoy this movie for most of the same reasons. I think it is really funny. So many of the interactions just make me laugh. I also found most of the characters very compelling. You root for the two main characters and despise the people you are supposed to despise. I also really liked how the movie manages to tackle more complicated issues such as miscommunication between cultures, conflicts within the family, and learning how to balance your own life with your relationship with your parents. I thought it handled these topics very well without getting too heavy-handed and preachy. Overall, I thought this was a very funny movie and a solid modern rom-com.


2020's

9. The Lost City

Kicking off the 2020s is The Lost City. This is an action-adventure rom-com starring Sandra Bullock and Channing Tatum. I really enjoyed the action-adventure part of the story but thought the romance section was well handled as well. I never knew how funny Channing Tatum was until I saw him in this movie. He and Sandra Bullock are great together and have so many funny moments where they just play off each other so well. Neither of these characters are your typical adventure heroes but they still manage to make it work in this movie. It was also fun to see Daniel Radcliff as the villain as I am so used to seeing him as Harry Potter. Sarah also really enjoys this movie and finds it very funny and re-watchable. 


10. Ticket to Paradise

Ticket to Paradise is the newest rom-com on this list. This movie follows Julia Roberts and George Clooney as they play divorced parents who must reunite to stop their daughter from having an impulsive wedding. This movie had a lot of fun moments in it. Both Julia Robert and George Clooney are very charming and have great chemistry together. I thought the setting of Bali was a lot of fun. There are so many great shots of the island scenery and does a great job of encompassing some island culture. While this movie is kind of like a tourism commercial for Bali, it still kind of works and makes for a pretty entertaining story. Sarah quite enjoys this movie as well as it is a bit of a throwback to the rom-com style that she likes. In the end, while not my favorite rom-com, it is still pretty entertaining to watch with Sarah. 

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