The Best Early ’00s Valentine’s Day TV Episodes

I’m in my romance era today, sure, but I’m also in my 2000s-TV-shows-that-changed-my-brain-chemistry era. They simply don’t make masterpieces like Gilmore Girls or Friends anymore. I mean, where are the zany and lovable small-town communities? How about the incest-y but unbreakable New York City friend groups? On a festive occasion such as Valentine’s Day, it seems only right to look back at the high art that raised us and introduced us to romance. Hey, maybe it was the relationships on these shows that made my love life what it is today. (I’m chronically single.)

I dare say Rory Gilmore’s relationships, the Rachel and Ross saga, and Seth and Summer’s magnetic connection are my Roman Empires. While it’s devastating that these shows ended a decade or two ago, they’ll always be in our hearts — and on streaming platforms, thank god. This holiday, I’m embracing nostalgia and presenting you with the very best early ‘00s Valentine’s Day TV episodes. I’m wishing you a day filled with chocolates, flowers, delightful TV, and hopefully no men who aren’t fictional.

The O.C. – “The Heartbreak”

I hope you’re mentally preparing for the Newport Beach Valentine’s Day Singles Benefit Dance right now. Let me help you get in the zone: Things are heating up between Seth and Summer, and they’re about to have a huge milestone moment. It’s important to note that the Ryan Adams cover of “Wonderwall” is involved. “I don’t know how it gets better than this.” – Taylor Swift

The Office – “Valentine’s Day”

Shocked and upset that I’m not entangled in a Dunder Mifflin office romance this Valentine’s Day. A girl can only dream… or watch this impeccably done episode so much that it feels like reality. You got Angela giving Dwight a bobblehead doll, Jan and Michael kissing in an elevator, Pam not having it when Roy offers her “the best sex of her life” as a gift, and more. Chef’s kiss.

Gilmore Girls – “A Vineyard Valentine”

Logan is no Jess. (Personally, I need a little edge, a little danger if you will.) That being said, Logan and Rory will always be an iconic Yale Daily News love story. In this quality episode, they make way too big of a thing out of Valentine’s Day. It’s weird, honestly. They invite Lorelai and her diner king BF, Luke, to celebrate the day of love at Logan’s family’s Martha’s Vineyard house. Needless to say, some family drama ensues…

Dawson’s Creek – “Valentine’s Day Massacre”

As someone who was once a ridiculously dramatic teen in a Massachusetts high school, this one hits home. This episode features Dawson taking his friends to a top-secret party hosted by a group with a bad reputation. The drama! Not to mention, Jen has a truly *unforgettable* first date with Henry. Yeah, I cannot wait to watch this for the 3,000th time.

Friends – “The One With The Birthing Video”

This episode of Friends truly lives rent-free in my mind. To jog your memory, Chandler thinks Monica gifted him with a porn video for V-Day — instead, he discovers a graphic video of live birth. Meanwhile, Joey is obsessed with Rachel and feels all the depression feels about it. Basically, if you’re looking for themes of unrequited love and the miracle of life (which I’m sure you are), you’re welcome.