What episode does Rory sleep with Dean in Gilmore Girls?

Over the course of seven seasons, Gilmore Girls had its fair share of controversial storylines. From Rory getting arrested and not speaking to Lorelai for months to Lorelai and Christopher getting married in the final season, some of these twists don’t sit well with fans.

But there are plenty more storylines that keep fans coming back to Netflix to binge-watch the beloved series over and over. Who doesn’t love watching the dance marathon episode, no matter how many times you’ve seen it? The Festival of Living Art? Sookie’s wedding? Classics!

One of the more polarizing stories to come out of the seven-season run of Gilmore Girls revolves around the reunion of Rory and Dean post-high school. After the chips have fallen with Jess (we know how that ended…) and Rory goes to Yale, she reunites with her first love.

If you’re wondering exactly when in the series Rory and Dean make the decision to reunite and sleep together, we’re sharing the episode number of the momentous occasion, along with background on the ensuing fallout from Lorelai. Buckle up!

What episode of Gilmore Girls do Rory and Dean sleep together?

In Gilmore Girls season 4 episode 22, titled “Raincoats and Recipes,” Rory and Dean act on their rekindled feelings for each other and have sex. Rory loses her virginity to her first love, a few years after they had broken up. In that sense, it’s romantic, however…

Earlier in season 4, Dean marries Lindsay and gets a job with a Stars Hollow construction crew (ironically working on the Dragonfly Inn). Throughout season 4, Rory and Dean reconnect and have a friendship, and it’s soon clear that there’s something more between them, especially to Luke, who knows Dean isn’t over Rory. His decision to drop out of college, causes the Doose’s outburst from Rory that catches Lindsay’s attention.

From there, Dean and Lindsay’s already tense marriage experiences more tension, and in spite of her insistence that Dean and Rory stop being friends, they still see each other. Rory even calls on Dean swoop in to save her from a bad date. When Rory and Dean ultimately sleep together in the season 4 finale, Dean was still married to Lindsay, though he claims their marriage is over.

Lorelai catches them indirectly, putting two and two together when she sees them alone and flustered in her house. Obviously, Rory isn’t thrilled that her mother isn’t thrilled, throwing the barb that she ruined Rory’s big moment of losing her virginity. But deep down, Rory knows that she partook in something that wasn’t completely without fault. It’s a tense situation that sees Rory through a period of reckoning in the beginning of season 5.

All seven seasons of Gilmore Girls and its miniseries are available to watch on Netflix.