Jess may not have been the best Gilmore Girls boyfriend, but he’s definitely the best ex-boyfriend

“Twenty-one Is The Loneliest Number,” season six, episode seven, originally aired 10/25/2005

Friends, we deserve this. After slogging through Rory’s poolhouse non-adventures for weeks now, this week we get a fancy party and a welcome character return. I understand that many of you may not agree with the second part of that statement. But we’ll get to the divisive character of Jess Mariano in a few.

First, have a Rory: a fizzy pink drink that’s like a My Little Pony in a glass, as we delve into Rory’s 21st brthday. This Amy Sherman-Palladino episode features some of her classic over-indulgences (Lorelai’s mad scientist Halloween plan) and effective moments that involve no words at all. For example: The look Lorelai gives Rory at the party upon learning that Paris is the new editor of the Yale Daily News. She alone knows how much that news must be killing Rory; Rory, revealed and flustered under her mother’s watch, quickly skirts off.

After all, it’s finally starting to dawn on Rory that there’s a reason why her mother fled from the Gilmore house as soon as she was able, even with a toddler in tow. Outfits laid out for her. Meals served. She’s not making any decisions about her now-flailing life, but in the opulent Gilmore house, she really doesn’t have to at all, and frankly, isn’t really allowed to.

It’s all the more painful that Richard is the one to realize how wrong this situation is, since it was his misstep—caving on Lorelai’s suggested tough love when Rory announced her intention to drop out—that caused this whole situation. his look of horror at the end of last week’s DAR gala is real: Rory is on the path to tossing all of her accomplishments and efforts to become the next wave of pampered Connecticut wives. It also makes sense that Emily is much less bothered by this development than Richard is, bringing Lorelai’s “new and improved Lorelai” taunt from the season’s first episode to light. Emily finally has someone to mold in her likeness, to create the perfect doting (grand)daughter that she can parade around to her friends, who isn’t about to mess everything up like Lorelai did with obnoxious T-shirts and caustic remarks. Oh, and the pregnancy: Emily’s comment that “we haven’t failed until that girl comes home pregnant” cuts Lorelai to the quick. Maybe she’s lashing out in hurt because Lorelai never told her about the engagement. Lorelai and Emily are caught in a cycle of bad behavior: They treat each other poorly because they treat each other poorly. One says something hurtful, the other one reacts, and the cycle continues ad infinitum.

Rory moving onto the Gilmore estate was an attempt for Emily to remedy all of that. And again, Lorelai’s wordless performance at the end, when she sees Rory walk into her 21st birthday not at an Atlantic City casino but at one of her parents’ opulent parties, is her worst fear come to light. I don’t even think she stopped to pick up her chocolate box.

“Let Me Hear Your Balalaikas Ringing Out,” season six, episode eight, originally aired 11/3/2005

I know it’s season six and all, but this is a magnificent episode, probably my favorite one Daniel Palladino ever did. In all fairness, I’ve written previously about the Jess parts:

But there’s so much more going on in this episode. The soccer subplot is pretty stellar, as is Lorelai’s new career as a color consultant. And again. Lauren Graham brings out all the chops for Lorelai’s breakdown over Paul Anka that is really a breakdown about the situation with Rory:

How could I have let this happen? How did I not see it coming? How didn’t I step in and do something? And why can’t I fix these things? I’m a bad mother!

It’s the ultimate challenge of parenting—one the Gilmores never learned—that your real job is to prepare your child as much as possible for their adult life. But just as important is letting go when the time comes. Lorelai is hoping against hope that Rory will come to the correct decision on her own, and knows she needs to stay away until then, but can’t help second-guessing herself on all the steps that led to this. The night Rory came home drunk in a tiara after breaking up with Dean, this path started to seem all but inevitable.

So Lorelai can’t talk sense into Rory, but at least there is someone around who can. Jess’ reappearance is the dose of reality that Rory needs to snap herself out of this Hartford dreamland she’s been living in. Only through his shocked perception of her current situation is she able to see how far she has strayed. When she quickly apologizes that the DAR is not a career, he scoffs, “of course not,” but the reality is that she could end up in the DAR forever, going straight from her grandparents’ house to a life as Logan’s wife, with never anything for her own. And the fact that he wrote a book is even more perfect; here’s Jess, with zero money, little support, no fancy school or college education, and he’s got a good job and has accomplished something. And all she has on her plate is orchestrating a Russian tea party the next day. Jess offers a clear lens into the Chilton Rory we remember (her reminiscences about those bus rides is a nice touch): wholly focused on grades and accomplishments, not reduced to Birkin bags and 15-course dinners and designated driving her drunk boyfriend and his idiot, inconsiderate friends. When she views herself how Jess sees her now, she barely recognizes herself.

That shock leads her to lash out at Logan, who, as he points out, never thought her dropping out would stick anyway. I have somewhat more sympathy for Logan in this episode on this rewatch: Yes, he is an absolute asshole to Jess at the dinner, but because he smartly and rightly views Jess as an actual threat. As Logan’s fun-times youth gets further winnowed away with each passing day, he clings to Rory as one of the only positives in his life: If Jess puts that in danger, and Logan’s had a few glasses of scotch, of course he’s going to lash out. Jess should understand that better than anyone; you could deliver some of Logan’s snide comments about high-school sweethearts and malt shops with equal ease. Still, it’s hard not to be as pissed at Logan as Jess is, as he cuts short the Rory and Jess reunion, but at least helps instigate Jess’ powerful queries about what’s really going on with Rory.

Logan is a big part of Rory’s unfortunate situation, so out he goes. Next up is her grandmother, who, with her slip of “when your father gets home” and trying to ground her 21-year-old granddaughter, lets her true feelings be known about Rory as a redo for Lorelai’s life. Rory may protest being grounded and saying she can go where she wants, but, as a guest in their house, she realizes she has little say in the matter at all. So, with this helpful push from Jess, Rory moves closer to stepping out of her grandparents’ life and back to her own. And not a moment too soon, at that.

Stray observations

• Rory and Lorelai’s original plan for her 21st birthday does sound pretty perfect.
• Best Gilmore outfits: Surprisingly, sequins! Emily’s silver jacket at the party and Lorelai’s short-sleeved sequin sweater with pencil skirt. Also, shoes! Lorelai’s lineup of shoes after Paul Anka pulls them all out is truly impressive. And Rory’s birthday party shoes with the ribbon ankle straps were even prettier than her dress.
• Worst Gilmore outfits: I know we’ve seen it before, but Logan’s frayed blazer bugs. It says, you can make me wear a jacket, but I’m still rebelling, man! Also, seriously, Lorelai, stop with the shrugs.
• I miss Halloween.
• This week in Gilmore entitlement: “We’re paying for these things!” Rory, you are paying for nothing.
• Ha, Katherine Thurston Moore. We see what you did there, ASP.
• Meta humor: “Girl Interrupted? Now that’s my idea of a feel-good movie.”
• Rory, I think you gave your virtue to Dean actually.
• Paris, what are the chances that food at Emily Gilmore’s house would suck?
• Remember when Tobey Maguire’s career was hot?
• Just when Finn couldn’t get any more unlikable, he disses INXS
• “You seem very obsessed with length.” EXCELLENT BURN.
• Next week: Enjoy the good times, because next week Christopher starts lurking around again. Also April shows up for the first time in the episode where Rory and Lorelai reunite. Like they couldn’t just let everything be happy for a single week.