When Harry Met Sally
This movie poses the perfect question for a romantic comedy: Can men and women ever just be friends? I have never learned as much about relationships as I did from this movie. It took me years of re-watchings to finally “get” the famous Katz deli scene. If you don’t know what I’m talking about, rent this movie, and prepare to laugh so hard you cry…and vice versa.

Sixteen Candles
This movie beautifully intertwines awkward encounters with genuinely touching moments. Molly Ringwald goes down in history as the nerdy girl hearthrob, and a generation of boys begin to put bets on romantic interests. All this and some cheesy 80s songs make for my favorite romantic comedy.

Breakfast At Tiffany’s
The original romantic comedy follows Holly Golightly (a socialite golddigger) through her many romantic escapades with relative strangers. She is a national icon, a naive, eccentric, attractive woman, who millions of cougars still follow to this day.

Bridget Jones Diary
What’s romantic about a slightly overweight, chain-smoking, alcoholic, British woman? A lot it turns out. This story revolving around a mentally unstable love triangle is loosely based off the novel “Pride and Prejudice” by Jane Austen. Don’t worry, this version won’t put you to sleep. The sad, frustrated anti-hero portrayed by Renee Zelwegger earned her a nomination for the Academy Awards that year.

Love Actually
The be all end all romantic comedy for a multitude of reasons. 1. It has nine vignettes about love. 2. It takes place during the holidays. 3. All the stories are intertwined. 4. Hugh Grant! 5. It features an elaborate kissing scene. All of this mixed with cynical British people puts this film at the top of the list.