Oh, boy. We’re at the middle of season two of Gilmore Girls with our supercaffeinated recaps, and we’re starting to hit the worst of times in Dean and Rory’s relationship. (Every time I rewatch this series, I forget how uncomfortable this part is.) Rory is starting to like Jess, and Dean’s getting super possessive. I want to tell him to calm down and back off. But then again, Lorelai basically told him to take it easy and he didn’t listen.

It’s not all teenage relationship drama. Richard made a bold decision, Jackson and Sookie took a big leap, and Emily had a meltdown about Christopher’s new girlfriend. These are my picks for highlights this time around.

An Elaborate Affair

I love Gilmore Girls. I love renaissance faires. Little did I know the two would mingle with “The Bracebridge Dinner.” Actually, renfaires come back into the story in later seasons–much to my delight. This time, the Independence Inn was set to host an over-the-top themed dinner for the Bracebridge group. However, the group who booked the dinner got snowed in (leading to the awesome Sookie quote pictured in the GIF above) and couldn’t make it. Their cancellation led to Lorelai hosting Stars Hollow pals plus Richard and Emily for the dinner instead.

This episode sticks out because of the silly but perfect theme. Since Stars Hollow has all kinds of wacky festivals, the idea of a Medieval Times-esque dinner fit right in and matched the tone. The other big highlight? Richard left his job. What we knew about Richard to this point was his dedication to tradition, to the tried and true. He’s the opposite of someone who’d rock the boat. That he was so unhappy he decided to leave behind the only job he’s ever had carried weight. He started the process of reinventing himself, and for Richard, it was about the most dramatic direction he could go in.

Favorite quote: “I have a New Year’s resolution for you—be more cynical and self-absorbed..” – Lorelai

Where’s My Basket?

Of all of Stars Hollow’s many traditions, the basket auction might be the best. And also, I maybe also said the same about the Firelight Festival. There’s just too much charm; I can’t help it. For the record, I think both sexes should be making baskets for the auction. Anyway, the celebration of the tradition in “A-Tisket, A-Tasket” introduced another Jess-shaped hiccup in Dean and Rory’s relationship. Jess bought Rory’s basket, and Rory—who so obviously wanted an excuse to spend time with Jess—stuck with the “It’s tradition!” argument in order to eat with him. It was a selfish move on Rory’s part, but if you’ve ever been in her shoes, you can relate—especially since Dean was acting jealous in a very unattractive fashion. I hate clingy Dean, and that’s become his general state of being. Ugh. He went to Lorelai to whine about Rory, for goodness’ sake. Not okay, Dean.

Putting stupid Dean aside, the episode had one particularly lovely moment: Jackson and Sookie got engaged. Some might think the way the engagement happened was boring or too simple, but it suited the couple to a tee. For the record, I’d consider marrying anyone who made a basket out of a stuffed pretzel bread.

Favorite quote: “As long as everything is exactly the way I want it, I am totally flexible.” – Lorelai

What Might Have Been

Christopher swept back onto the scene in “It Should’ve Been Lorelai,” and he brought his long-term girlfriend Sherry with him. Oddly enough, he forgot to mention to Lorelai and Rory he was traveling with Sherry. Uh-huh. The best word to describe Sherry is probably intense. She was too overbearing to be likable, and she tried too way hard with Rory. As amusing as it was to watch Rory and Lorelai wrangle Sherry, the real fun came with Friday night dinner.

Sherry took Rory away from Friday night dinner, and Christopher went with Lorelai instead. You’d think Emily would have been happy about seeing Christopher but nope. Instead, she freaked out about Sherry in the most Emily Gilmore way possible: she was angry Sherry is the one who inspired Christopher to reform his life and not Lorelai. Way to make Lorelai feel awesome about herself, Emily! It’s one of those moments that set back any positive thoughts you might have had towards Emily.

Lorelai didn’t come out so favorably either. At the end of the episode, she told Christopher she was finally letting him go and indirectly blamed him for her years of failed relationships. It was a dick move on par with Emily’s actions. These Gilmores.

Favorite quote: “No two people know more about assisted suicide than the two of us. Kevorkian called today for a couple of tips.” – Rory

Are you playing along at home? Which episodes from the middle of season two would you highlight? Shout them out in the comments.

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IMAGES: Warner Bros., Katie, Forever Young Adult, Gilmore Gifs