Romantic comedies to sweeten your Valentine’s Day


Photo via Disney

As a pretty big romance fan, I enjoy looking into and watching a variety of movies in the genre, especially on Valentine’s Day. Though I love most of these movies, I particularly enjoy romantic comedies set in the 90s or early 2000s. These are a few of my recommendations.


      “Drive Me Crazy” (1999)

  This movie revolves around popular and preppy Nicole Maris (Melissa Joan Hart) and her troublemaker next door neighbor, Chase Hammond (Adrian Grenier). The two main characters are both recently single after being flaked on by their respective romantic partner right before the upcoming centennial dance. To combat the prospect of being socially ostracized, Nicole talks Chase into taking her to the dance and hanging out with her prior in order to make their exes jealous. 

I didn’t have high hopes for this movie and definitely had my worries going into it. I thought the movie would move too slowly, completely change the characters’ personalities by the end and lead up to something not worth rooting for. However, I was pleasantly surprised and found this movie to be something I could watch again and still feel entertained. You can find this movie on Apple TV, Amazon Prime Video and YouTube.


      “Clueless” (1995)

  “Clueless” follows the incredibly popular and self-involved Cher Horowitz (Alicia Silverstone) as she plays matchmaker for those in her school, including her new ‘out of touch’ friend, Tai (Brittany Murphy). Cher begins feeling jealous toward Tai as she climbs up the social ladder and eventually begins to grow even more popular than her. Upon being treated differently, Cher begins rethinking her past behaviors and treatment of others, including her relationship with her ex-stepbrother, Josh (Paul Rudd). 

This movie definitely had its questionable aspects; however, I’ve always enjoyed Cher’s personality and interactions with others, along with her style. Watching the character development between her and other characters makes this movie an entertaining watch. This would be great for something to watch on Valentine’s Day that isn’t full of downhearted spirit. “Clueless” is available on Hulu, HBO Max and Apple TV.


   “A Cinderella Story” (2004)

  As you might be able to tell from the title, this movie puts a modern twist on the classic Cinderella story. It features socially-ignored teenager Sam Montgomery (Hilary Duff) who is  forced to work at the diner owned by her stepmother, Fiona (Jennifer Coolidge) after the death of her father. Throughout this, Sam is messaging an anonymous boy who goes to her school that she met in a Princeton chat room. The two decide to meet at the upcoming Halloween school dance when she realizes the mystery man she’s been talking to is none other than Austin Ames (Chad Michael Murray), the most popular guy in her school.

I watched this movie for the first time about five years ago, and since then, I’ve rewatched it countless times and always felt it to be great for Valentine’s Day. This movie can be found on HBO Max and YouTube TV.


  To an extent, all these movies feel cheesy and cliche with enough comedy and romance to keep you interested, laughing and anticipating the next move. These factors all contribute to making the viewer feel the way Valentine’s Day is depicted, making these films a great watch for the occasion.