With fall comes a certain nostalgic need that can only be met with heartwarming, albeit somewhat cheesy, romantic comedies.

I want to laugh, smile and cry while taking in the city streets of New York, Chicago and whatever other major city that the unlikely love story takes place in. Now listen, I’ve watched a lot of romantic comedies in my day but these listed take the cake for me. You cannot convince me that there is anything better than rom-coms created between 1990 & 2009. If you haven’t watched them, you must. And if you have, rewatch them again and again because every time you do you’ll be taken to a happy place and you’ll notice new fun details and jokes and things that when you see them in real life, will make you smile. Life is hard and it’s important that we take time to take part in things that bring us joy and flood back good memories. Movies and television may not be the healthiest coping mechanism but they do the trick sometimes. And with that, I will do my best to bring you a list of books as soon as I take the time to read what has been on my list and share a healthier way of being transported with you.

The Best of the Best

Hover to see where you can watch for free right now (as of Oct 2021).

Honorable Mentions

La La Land

Sleepless in Seattle

Maid in Manhattan

Confessions of a Shopaholic

Runaway Bride

My Best Friend’s Wedding

Failure to Launch

The Holiday

The Ugly Truth

Can’t Buy Me Love

Dirty Dancing

Sixteen Candles

13 Going on 30

Notting Hill

Happy Watching! - Riley