The Best Rom-Com's to Cure Your Valentine's Day Loneliness
- Paige Venable
- 11 hours ago
- 10 min read
Rowdy staff members share their thoughts on iconic rom-coms.
By: Paige Venable
Valentine’s Day is right around the corner. For some, that’s a good thing. It means they have an excuse to spend time with their significant other on the most romantic day of the year. On the other hand, there are several single individuals — myself included — who have yet to figure out what their Valentine’s Day plans will be.
As much as I truly enjoy being single, especially considering the dating scene in Gainesville, I’m a sucker for romantic comedies. They perfectly show how no two love stories are exactly the same and that true love is really out there.
In an attempt to cure your Valentine’s Day blues, I decided to curate a list of the most iconic rom-coms that are a must-watch this time of year. To make it even better, I also asked the Rowdy staff their honest thoughts about the movies on this list to help you narrow down your options.
1. “10 Things I Hate About You” (1999)
Trope: Enemies to Lovers
Main Characters: Kat Stratford (Julia Stiles) and Patrick Verona (Heath Ledger)
Where do I even begin? Ironically enough, I watched this movie for the first time on Valentine’s Day in 2021 and have seen it at least five times since. It’s just THAT good. “10 Things I Hate About You” is a modern twist on Shakespeare’s “Taming of the Shrew”, which makes it that much more perfect. While Kat and Patrick’s chaotic, yet entertaining, dynamic is the focal point of the film, it also highlights Cameron’s strategic plan to win over Bianca. For context, Bianca is Kat’s younger sister who has always dreamed of finding her true love. Meanwhile, Kat has a much more pessimistic perspective on young love.
The film moves very fast — and there’s never a dull point. Overall, “10 Things I Hate About You” is amazing all around and I have absolutely zero complaints. Oh, and also, the poem scene will never get old.
Rowdy Rating: 4.429 hearts
“I love the fact that it’s a retelling of ‘Taming of the Shrew’. I think that movies that can completely modernize an old story are so fun and creative to watch. I also love the fact that the leads are a totally unpredictable couple that don’t really follow any stereotypes.”
“She’s mean to him and he’s still such a sweet and respectful guy to her like lmfao #need.”
“I love that they find love when they weren’t even looking for it. I love their fun dynamic and that they allow each other to be the truest version of themselves.”
2. “13 Going on 30” (2004)
Trope: Best Friends to Lovers
Main Characters: Jenna Rink (Jennifer Garner) and Matt Flamhaff (Mark Ruffalo)
Jenna and Matt walked so Poppy and Alex could RUNNN (if you get that reference, I love you). Rewatching this movie a few months ago made me realize how much I love the “best friends to lovers” trope. It seriously doesn’t get better than Jenna and Matt. From the start, it’s painfully obvious that he is obsessed with her and would do literally anything for Jenna. She can do no wrong in his eyes. However, when they were teenagers, Jenna never saw Matt as more than a friend, so he assumed it would be impossible for them to be together.
Fast forward to when they’re both 30, it seems as if everything has changed and maybe he was the right choice all along. That said, Jenna makes it her mission to win her best friend back — and this time, she hopes it’ll be more than platonic.
“13 Going on 30” is a 2000s classic and the vibes are immaculate. Not to mention, we LOVE to see a man yearn.
Rowdy Rating: 4.058 hearts
“I love the way it portrays the loss of innocence, coming of age, preserving one’s inner child, and listening to your heart rather than pretending to be someone you’re not!”
“It’s such a nostalgic classic, and seeing it when I was younger made it more relatable. It made me really want to appreciate being in the present and also excited for when it is my turn to be in my 30s.”
“This is one of my favorite movies ever!! …It reminds me of the importance of appreciating every stage of my life and taking my time to grow up. It’s also a good reminder of why the ‘stud’ boyfriend isn’t always the best choice LOL.”
3. “27 Dresses” (2008)
Trope: Enemies to Lovers
Main Characters: Jane Nichols (Katherine Heigl) and Kevin Doyle (James Marsden)
One of the most underrated rom-coms of all time is “27 Dresses”. The movie follows Jane, who is known for being a professional bridesmaid and always putting the needs of others before her own. While she is initially head over heels for her boss George, her feelings for him slowly fade as she realizes that their relationship can be nothing more than platonic. In the meantime, Jane becomes fond of her (once) enemy, Kevin, who turns out to be more tolerable than she initially thought.
I love how this movie emphasizes the importance of acknowledging your own needs instead of always putting yourself last. Spoiler alert: Kevin may or may not be the one who helps Jane realize the significance of this concept.
I could watch this movie over and over and never get tired of it. Also, if you love Elton John, pay attention to 1:08:31…you’ll thank me later.
Rowdy Rating: 4.125 hearts
“I love that she’s always underestimated. She thinks that she is typically not the main character, but he sees her as more.”
“It’s the perfect movie for any girl who never does anything for herself. The ‘Benny and the Jets’ scene is peak romance.”
“Bennie and the Jets’ scene.”
4. “A Cinderella Story” (2004)
Trope: Anonymous Love
Main Characters: Sam Montgomery (Hillary Duff) and Austin Ames (Chad Michael Murray)
“A Cinderella Story” is a modern take on the iconic Disney tale, “Cinderella”. This movie holds a special place in my heart because it was one of the first rom-coms I watched as a little girl. Although there have been multiple renditions of this film, nothing beats the original. “A Cinderella Story” also includes such cute references to the original plot of “Cinderella,” which make it all the more wholesome.
All things considered, Hillary Duff gave the perfect performance and Austin Ames is Chad Michael Murray’s best character to date.
Rowdy Rating: 3.417 hearts
“Bring back Disney Channel rom-coms. It’s a classic story that everyone knows the ending of, but it’s always entertaining to watch. and Chad Michael Murray was great in it.”
“Chad Michael Murray, I love you.”
“I love the Y2K aesthetic, like her phone being her glass slipper is actually hilarious work.”
5. “How to Lose a Guy in 10 Days” (2003)
Trope: Bet/Hidden Agenda
Main Characters: Andie Anderson (Kate Hudson) and Ben Barry (Matthew McConaughey)
“How to Lose a Guy in 10 Days” is arguably one of the most popular rom-coms of all time. One of the main reasons I enjoy this movie is because it’s such a unique trope that is perfectly brought to life by Kate Hudson and Matthew McConaughey.
It’s also hysterical the entire time, and never fails to make me laugh. While the plot is very chaotic, that only adds to the charm. The couple’s counseling session with Andie’s best friend is true comedy. Definitely a must watch on Valentine’s Day!
Rowdy Rating: 4.50 hearts
“I love how both of them are insane. Her job is so chic and the NYC backdrop just adds to it. I also just love the part where he takes her to meet his family.”
“I love that they try and trick each other and end up falling in love with the real version of themselves. You can tell from the moment he sees her that he’s head over heels.” Love this quote.
“I LOVE that it shows that people will always resort to being themselves, and are usually loved most for it. While the two main characters were trying to put on these fake personas, they found the most connection and chemistry when being themselves.”
6. “Legally Blonde” (2001)
Trope: Friends to Lovers
Main Characters: Elle Woods (Reese Witherspoon) and Emmett Richmond (Luke Wilson)
Elle Woods is THE law school icon that we all love and adore. I first watched “Legally Blonde” when I was a young girl and, I kid you not, it made me want to be a lawyer at the time. This movie is perfect in every single way.
Elle initially decides to pursue law school in hopes of winning over Warner, her ex-boyfriend who broke up with her before he started at Harvard Law School. However, after choosing to pursue law school and challenging herself academically, she realizes her true potential. Elle learns to value her worth and be the independent, iconic diva we all know and love.
While “Legally Blonde” is technically considered a rom-com, it more importantly emphasizes the significance of realizing your true potential as a woman and chasing your dreams. However, I had to include it because Elle is not only amazing, but because Emmett compliments her so well. We all knew Warner was never the right choice anyway…
Rowdy Rating: 4.444 hearts
“Elle Woods is the original girlboss and I love how she’s a girl’s girl!!!!! My favorite part is when she finally befriends Vivien rather than blaming her for her problems (when know the bonehead Warren is to blame for everything).”
“MY QUEEN, MY MONARCH, MY EVERYTHING…ELLE WOODS…talk about academic diva like this isn’t even a rom-com for me this is a documentary of female excellence like that’s my lawyer fr.”
“It’s a nice reminder that sometimes our desperate search for external validation is actually what’s holding us back from achieving our full potential.”
7. “Love Actually” (2003)
Trope: Multiple
Main Characters: Prime Minister (Hugh Grant) and Natalie (Martine McCutcheon)
“Love Actually" perfectly encapsulates the idea that every relationship is unique and special in its own way. This movie follows a total of nine different plotlines, making it somewhat chaotic, but that’s part of the excitement the movie brings. Each dynamic shows how love can be complicated, but the experience is always worth it in the end.
While “Love Actually" does take place around the Christmas season, who said you can’t enjoy watching it on Valentine’s Day?
Rowdy Rating: 3.50 hearts
“LOVE IT because it shows so many different aspects of love and finding love.”
“Every storyline is so uniquely funny and lovable. Colin Firth’s storyline melts my heart every time.”
“Love the part where Hugh Grant dances around the British White House.”
8. “Love, Rosie” (2014)
Trope: Best Friends to Lovers
Main Characters: Rosie Dunne (Lily Collins) and Alex Stewart (Sam Claflin)
Oh my gosh. “Love, Rosie" has to be one of the most insane rom-coms I’ve ever seen, but I promise that it is SO worth the watch. The way that Rosie and Alex are horrible at communicating their feelings to one another, but still manage to find their way back to each other is what makes this movie one of my favorites.
The first few times I watched this movie, I didn’t even realize that the reason Alex never confessed his feelings was the aftermath of Rosie’s 18th birthday party. When he finally tells her at the end that he’s been the one girl he’s wanted his entire life — PEAK. If you want to see a man YEARNNN, you must watch this movie. Sam Claflin, you never fail to amaze me.
Rowdy Rating: 3.875 hearts
“STOP SO CUTE IN ALL WAYS.”
“Sam Claflin 😍😍😍"
“A friends-to-lovers masterpiece. The yearning in this movie is unbeatable.”
9. “Set It Up” (2018)
Trope: Enemies to Friends to Lovers
Main Characters: Harper Moore (Zoey Deutch) and Charlie Young (Glen Powell)
“Set It Up" is one of the best newer rom-coms that’s been released within the past 10 years. While most recent movies have tried, and unfortunately, failed at the rom-com formula, "Set It Up” got it just right.
Harper and Charlie aren’t necessarily fond of each other at the start, but the more they spend time with one another, the more the pair realizes that they’re more alike than they thought. Their brave attempt to get their bosses to fall for one another ultimately leads them to form a beautiful relationship of their own. Zoey and Glen also have unbeatable chemistry, which keeps you glued to your seat the entire time.
Overall, this rom-com is a perfect balance between romance and comedy, as you are guaranteed to laugh multiple times while watching.
Rowdy Rating: 3.60 hearts
“I love the acting in this movie. It is fun and romantic at the same time. Their chemistry is off the charts and it shows an unlikely pair coming together. It shows how they also change their own lives for good.”
“Me, personally, I just like workplace romances cause, like, yes! Be employed!”
“Glen Powell’s face. Also, while it’s hard to avoid clichés in a rom-com, this one does a good job of really leaning into the tensions between the characters and not shying away from how different personalities don’t always click at first.”
10. “When Harry Met Sally" (1989)
Trope: Friends to Lovers
Main Characters: Sally Albright (Meg Ryan) and Harry Burns (Billy Crystal)
A list of rom-coms wouldn’t be complete without "When Harry Met Sally". When the movie starts, you think that there is no chance that Sally and Harry could ever end up together. On one hand, Sally has a very Type A personality and is an optimistic woman who knows what she wants. On the other hand, Harry is extremely pessimistic and seems to have a comment for every single thing Sally says or does. However, as time progresses, they both let their guards down and allow themselves to connect with one another on a deeper level.
“When Harry Met Sally" is a classic and a must-watch movie during the Valentine’s Day season.
Rowdy Rating: 4.357 hearts
“The entire feel of this movie is just wonderful. It’s the perfect autumn/winter watch, and the camera quality makes it even better. All the characters in this movie are so well developed and beautifully written. I find myself hoping that they will end up together every time.”
“Such a classic. Every scene blends into the next as you slowly watch them fall for each other whether they realize it or not. The classic friends to lovers slow burn.”
“I love a friends-to-lovers movie that spans over a decade. This movie is also hilarious–the diner scene is one of my favorite movie clips ever.”
While I would argue that the list above has some of the best rom-coms of all time, I also asked the Rowdy staff to provide other options that could be perfect for your Valentine’s Day.
Extra Rom-Coms to Watch:
“Moonstruck” (1987)
“Say Anything” (1989)
“Muriel’s Wedding” (1994)
“Never Been Kissed” (1999)
“Serendipity” (2001)
“The Confessions of a Shopaholic” (2009)
“The Proposal” (2009)
“Crazy Rich Asians” (2018)
“Sweethearts” (2024)
All things considered, I wish you all the best Valentine’s Day and hope that my suggestions can help make it even better. Whether you're in a relationship or single this time of year, it’s always important to remember that love is a special emotion that shouldn’t be taken for granted.
Not only that, but love doesn’t just have to exist within romantic relationships. Rather, some of the best love comes from our platonic relationships with friends and loved ones. Love is truly beautiful, and when you find it, platonically or romantically, remember to cherish it. Happy Valentine’s Day <3
Paige Venable is a junior studying accounting with a minor in public relations. When she’s not busy with school work, she loves rewatching her favorite tv shows, online shopping, and going on walks!