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Episode 2 - Rory's first day at Chilton Prep begins badly when Lorelai accompanies her daughter into the intimidating school wearing a T-shirt, cut-off jeans and cowboy boots, an outfit that draws disapproving stares from the other mothers.

Episode 3 - Rory and her grandfather enjoy a glorious day of golf, making Lorelai feel left out and the inn hosts a double wedding with two sets of identical twins.

Episode 2 - October 12, 2000 | The WB

Episode 3 - October 20, 2000 | The WB

• Lauren Graham as Lorelai Gilmore
• Alexis Bledel as Rory Gilmore

Lorelai is doing Rory’s nails. Why? Because tomorrow is Rory’s first day at Chilton! Nothing can ruin this.
Except… sleeping in.

Rory wakes Lorelai up at 7:10, and they are up against it. The only clean thing Lorelai has to wear is her Dukes of Hazzard look—and she has to go inside and meet the headmaster. Naturally, it takes about two minutes for a dad to hit on her. When they finally make it to Headmaster Charleston’s office, Emily is already there waiting. She insists Lorelai take off her jacket, and Lorelai immediately regrets it.

Lorelai heads back to Stars Hollow, where everyone is shocked by what she wore to Rory’s first day of school.

Meanwhile, Rory’s first day is off to a rocky start. The classes are hard, she’s greeted very coldly by a girl named Paris, and she’s aggressively hit on by a dude named Tristan.

Back at the Inn, Lorelai is stunned to see the Chilton dad again—he’s shown up to ask her out. She shuts it down immediately; dating a Chilton dad would be way too complicated.

While trying to open her locker, Rory accidentally bumps into Paris, who’s carrying a project for their next class. The teacher tells Rory she has to help Paris, but Paris flat-out refuses. Starting to think maybe Paris doesn’t like Rory.

Lorelai gets a call from her neighbor Babette saying someone is at her house installing internet. Lorelai did not order internet. Turns out Emily did. Lorelai tracks her down and tells her that paying for Rory’s school does not give her the right to meddle.

After school, Lorelai and Rory walk through Stars Hollow, and Lorelai asks Rory if she thinks Luke is cute. Rory says Lorelai can’t date Luke because his food is too good—and a breakup would ruin everything.

It’s time for another Friday night dinner. Emily and Richard tell Rory she should join Richard at the club to golf. Lorelai is not thrilled that they blindsided Rory, because of course Rory wouldn’t say no to her grandfather. Things start off awkward, but they end up having a really great time. Rory learns more about Richard, and Richard learns more about his granddaughter.

Later, Lorelai is shocked to find out Rory actually had fun. To make matters worse, Richard calls Rory the next day. When Lorelai floats the idea of skipping Friday night dinner, Rory says she doesn’t want to. Lorelai is clearly bothered by Rory growing closer to her grandparents and picks a fight over Rory borrowing her sweater without asking.

They make up, and Lorelai explains that just because she doesn’t have a good relationship with Richard and Emily doesn’t mean Rory can’t.

When they arrive at Friday night dinner, Richard and Emily are thrilled to see Rory—once again making Lorelai feel left out.

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