10. “10 Things I Hate About You” (1999)

In this popular classic, a young Heath Ledger attempts to woo Kat Stratford, a moody and abrasive teenage girl with little interest in the possibilities of young love. If you’re into the “chase” and being serenaded with a cringe rendition of “I Love You Baby” by Frankie Valli at a high school soccer practice, then this one’s for you. 

9. “Maid in Manhattan” (2002)

Starring Jennifer Lopez as the Maid in Manhattan, this rom-com tells the story of how a single mother catches the eye of a well-known politician after trying on a hotel guest’s Dolce and Gabbana jacket. Suddenly tangled up in a mess of lies, the “Maid in Manhattan” attempts to keep her identity a secret, while remaining true to herself. This reimagined modern depiction of Cinderella is sure to keep your “rags to riches” hopes alive. 

8. “My Big Fat Greek Wedding” (2002)

Toula Portokalos struggles to earn her family’s approval when she accepts a marriage proposal from a man outside of her Greek heritage. Determined to follow her heart, Toula seeks to integrate both cultures into her wedding day, but her family has other ideas; anyone with a culturally proud family will get a kick out of this mess. 

7. “The Break-Up” (2006)

Break-ups can be tough, especially if you and your partner are living together. Brooke and Gary take on this endeavor after they break up and refuse to move out of their shared apartment. While they agree to transition their relationship to roommates, tempers flare as their lives drastically change–especially after Brooke kicks Gary off their “couples-only” bowling team. Filled with ups and downs, The Break-Up will keep you rooting for that obvious, broken relationship.  

6. “Enchanted” (2007)

What are the chances that after falling through a mystical, animated wishing well from a fairytale land to the streets of New York City, you would run straight into the arms of a single Patrick Dempsey? Reality-stricken Gisele grapples with these strange surroundings as she waits for her true–love Edward to leave the magical land of Andalasia to come and rescue her. Accompanied by an original soundtrack, “Enchanted” is a wake-up call if you’re looking for your happily ever after in all the wrong places.  

5. “Love, Simon” (2018)

Based on the bestselling novel by Becky Albertalli, “Love, Simon” explores Simon Spier’s hesitance towards coming out to his family and friends; however, this changes once he begins messaging “Blue”, an anonymous gay student at his school. Tasking himself with discovering Blue’s identity, Simon reevaluates his own amongst the chaos of everchanging high school relationships. “Love, Simon” is truly a coming-of-age story for us all. 

4. “Letters to Juliet” (2010)

Verona, Italy plays homage to Shakespeare’s Juliet with a timeless tradition in which people can leave letters for the fictional character, asking for her help. Claire did just that in Letters to Juliet, but it wasn’t until Sophie found her letter nearly 50 years later that she finally received an answer. Inspired by Sophie’s heartfelt response, Claire embarks on a journey across Italy to find Lorenzo Bartolini, a boy she once planned to run away with, along with Sophie and her overprotective grandson. To never forget  your first love comes in handy on this adventure, especially once the three of them discover 74 different Lorenzo Bartolinis. 

3. “That Awkward Moment” (2014)

There comes a time in every relationship when both parties must ask themselves, “so . . .where is this going?” While Jason has never fared well in these conversations, lucky for him, he soon agrees to remain single with his best friends Daniel and Mikey, after Mikey’s wife requests a divorce. However, despite this pact, all three of them find themselves getting caught up in relationships, rapidly approaching That Awkward Moment conversation. You’ll never find a dull moment with this rom-com; it fully delivers on the comedy, with romance as a bonus. 

2. “Sleepless in Seattle” (1993)

Sam Baldwin delivers a scene of raw emotion after his son Jonah calls a radio show on Christmas Eve and gets stuck telling Dr. Marsha Fieldstone how deeply he loved his late wife. Suddenly, every woman in America is in love with Sleepless in Seattle, including Baltimore native Annie Reed. Love knows no distance in this celebrated classic and is a must-watch for your next movie night. 

1. “How to Lose a Guy in 10 Days” (2003)

If you’ve done everything right and still haven’t found “The One,” you might consider an alternative approach. Andie Anderson puts Benjamin Barry through the wringer as she attempts to “lose him” as inspiration for her magazine article entitled “How to Lose a Guy in 10 Days.” Conversely, Barry has taken on his own challenge: get a girl to fall in love with him in 10 days. As each other’s goals are unbeknownst to them both, this romantic comedy serves up the drama, along with Kate Hudson’s iconic yellow dress.