Chris is wearing what appears to be a very normal black buttondown and jeans, but Lorelai assures him that it's all wrong: "It's very Joaquin-Phoenix-at-the-Oscars." Christopher: "I have no clue what that means. Why are you grimacing at this shirt?" He gets pissed that Lorelai keeps saying "man date," and points out that it shouldn't matter what he's wearing, since he's just going out to "have a beer with a farmer." She says she just wants him to make a good impression, but he wonders what she's worried about, considering how well their walk through town went. "Eh," Lorelai shrugs. "What are you saying?" asks Christopher, worried. "I'm saying it didn't go so great," Lorelai tells him. Chris: "But...the wagon!" Lorelai: "Was full of cleaning supplies and shoe trees!" She says that when some other couple got married, their wagon was full of handmade clothing and bookends whittled into the shapes of Senegalese tigers: "That's a Welcome Wagon. We got a 'We're Tolerating That You're Here' Wagon. Sorry." Christopher is disappointed: "So, going out with Jackson is important because...?" Lorelai says it's important because Jackson is loved and respected: "If you're in with Jackson, you're in with Stars Hollow." Christopher sighs. He guesses he can wear the gray polo shirt. "I love that idea!" Lorelai cheers. He asks if his jeans are okay. Well...Lorelai breaks it to him that they're a little tight. And then, well, his shoes.... Christopher sighs again: "I hate to say this out loud, but all of a sudden I'm very nervous about my man date with a farmer." Hee. Lorelai says that he's going to be fine, and as he goes up to change, she reminds him, "Not too much stuff in the hair!"
The man date has begun. Jackson asks Chris what he thinks of the joint. Christopher says it's great. "Not exactly a Manhattan hot spot," Jackson needles, and Christopher points out that the beer tastes just as good in Stars Hollow as it does in Soho. He's giving it his best shot to make a good impression, asking Jackson about his crops. Apparently it's been an excellent eggplant year; Jackson assures him that he's Christopher's eggplant connection. "Guess I'll have to get rid of my other guy, then," Christopher jokes. Jackson doesn't laugh. Awk...ward. They watch some basketball for a second, and Jackson finally makes his move: "So, you and Lorelai, huh? Quite an achievement. Many have tried, many have failed." Chris makes some noises in agreement. Jackson gives him a long, hard look and drops some metaphorical action on him. He says that what he loves about farming is the commitment: "You have to be there 24/7 for your crops, no matter what. You can have the greatest soil, and perfect seeds, but if you don't have the commitment, you won't get good results. No shortcuts, no quitting." Christopher may be a Backstreet Boy, but he gets it: "It's a lot of responsibility," he agrees, knowing they're talking about Lorelai. "You must really love farming." Jackson: "I do. Sookie and I, we both do." Christopher: "I do, too."