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At the request of leading citizen Debbie Fincher (Heidi Swedberg), Lorelai (Lauren Graham), and Luke (Scott Patterson) agree to talk to the Stars Hollow High School students on Career Day. When it turns out the kids are less interested in Lorelai's business advice than in the fact that she'd been an unwed teen mother, she delivers a lecture that no one will ever forget! Elsewhere, Lane defiantly vows to dye her hair purple upon finding out that her mom wants to send her to an ultraconservative religious college; and erstwhile sweethearts Jess (Milo Ventimiglia) and Shane (Jessica Kiper) make public spectacles of themselves, arousing not only Luke's (Scott Patterson) anger but also Rory's (Alexis Bledel) not-so-suppressed feelings toward Jess.