Episode 16 of "Gilmore girls"
s01e16 Star-Crossed Lovers and Other Strangers

Luke's ex-girlfriend Rachel arrives in Stars Hollow unexpectedly, and immediately picks up on the attraction between Luke and Lorelai, which they deny. Rachel decides to stay for awhile, which leaves Luke and Lorelai with mixed feelings. Lorelai and Rory are amazed when Emily agrees to excuse Rory from Friday night dinner so that Rory and Dean can celebrate their three month anniversary. When Lorelai arrives for dinner, she discovers the source of Emily's largesse -- her mother has invited another guest -- a man with whom she secretly hopes to fix Lorelai up. After a painful dinner with one of the world's most boring men, Lorelai attempts to escape through the window of her old bedroom, but is caught in the act by Richard. When he is forced to admit that even he is bored by the man, he uncharacteristically covers for her and lets her make her getaway. Back in Stars Hollow, Dean treats Rory to a wonderfully romantic dinner, and then gives her a present -- a car that he's restoring for her. As they sit in the car, Dean professes his love, but Rory is unsure how to respond. Crushed, Dean breaks up with Rory, who is heartbroken.