Next night. Rory sits on Lorelai's bed reading a book, as Lorelai is going through her entire wardrobe looking for something to wear. Rory tells Lorelai to wear the dress she picked out that morning, but Lorelai knows that morning butt and evening butt aren't the same butt. Rory tells Lorelai to hurry her butt because Payton's picking her up any minute. Lorelai comes out in a brown-on-brown outfit that's got puffy shoulders. Rory tells her she looks fantastic because Lorelai told her to say that. Lorelai finds some flimsy scarf-looking thing on the floor, calls it a shirt, and decides to change. Rory finds a necklace as Lorelai changes. Rory slowly picks out a necklace as Lorelai worries that this guy isn't as attractive as she remembers, since the lighting was "so-so" in the auction and she only saw him for a few minutes. Rory's still picking out a necklace as Lorelai babbles that the mind plays tricks on you when you're bored. Then Rory tells Lorelai that she liked the other outfit more, so Lorelai calls Rory evil. Blah blah blah blah boring boring blah. Then they suddenly hear the car pull up. They're impressed with Payton's car.
Downstairs, Lorelai tells Rory that if this guy sucks, Rory will fake a fever in an hour. Lorelai opens the door, turns back around, and says, "You're feeling just fine." Lorelai introduces Payton to her daughter Rory, and somehow there's not one flinch of shock or surprise at meeting a sixteen- (or probably seventeen by now, right?) year-old girl. He's like, "Hey!" as if all the women he dates have children preparing to go to college. Lorelai tells Rory not to wait up and to limit her guests to only two or three crackheads, since they eat all the good cereal. Payton tells Lorelai that she looks wonderful (can you not hit on her in front of her kid, please?), and Lorelai is forced to say this clunker of a line: "Oh. So do you, Payton. So do you."
Later, Rory is asleep when Lorelai comes home. She wakes Rory, who asks what time it is. It's 10:15. Since when does Rory go to bed so early? Shouldn't she be up studying? And why wouldn't she have CuteDean over when she's got the house to herself all night? Why haven't we done the episode where Rory panics over her virginity or CuteDean starts to get pissed that it's been two years without anything other than kissing or at least address the fact that maybe Rory doesn't want sex because she doesn't want to turn into her mother? Something. Anything. This kid's seventeen or whatever and never wants to do anything bad, nor has she had one dirty thought. I'm not buying it anymore. Anyway, Lorelai hated the date that we didn't get to see. Apparently, Payton didn't have a personality or a sense of humor (what happened to that cute wit you were just gushing over, Lor?). She complains that all he did was talk about his car. He was boring as he told her everything she might ever need to know about a Jaguar. Maybe he was nervous, Lorelai. It was a first date. Maybe you were gushing about his fancy rich car so he started talking about it. Then Rory and Lorelai complain about people who like wine, and who spend time choosing the wine. Lorelai chimed in with a story about puking on cheap wine in the ninth grade and was mortified to see that he's not really interested in her story about puking at fourteen. Maybe because he figured out in one story why you've got a high-school senior at your house. Rory's shocked that Payton wasn't charmed by Lorelai's wine puke story. "I know!" Lorelai Monicas. She says she spent the rest of the date wondering about the kid she puked on way back when. Rory asks if the food was good, at least. "Tiny portions; weird sauces," Lorelai moans. And free. It was free, right? Lorelai says she's off to bed. Rory asks if she's still going to the Bowie concert. Lorelai says there isn't a way she could stand Payton for another night. Wow. You don't get many chances to win Lorelai's good graces, huh? Lorelai tells Rory that tomorrow she'll teach her all she learned about being a pilot. Poor Payton. Maybe I'd have less sympathy for him if we got to see the stinker of a date ourselves. It's not like Lorelai's had even an ounce of romance in a while.