An Affair to Remember

S4 E6: When Emily plans an elaborate launch party for Richard's new company, she hires Lorelai and Sookie to cater the affair but insists they prove that they are worthy of her trust. After Richard's partner, Jason "Digger" Stiles, insults Emily by suggesting that her party idea is outdated, Lorelai confronts him and is surprised when he asks her out to dinner. Meanwhile, Rory has a tough time finding a decent place to study at Yale.