Lorelai accepted Max's proposal, but soon before the wedding, she realized she didn't feel right, so they broke up. She and Su Qi were excited about opening a shop in a dilapidated independent hotel, but the boss refused to sell it. Su Qi is engaged to local farmer Jackson. Luke's teenage nephew Jess Meliano lives under his care. Jess felt unhappy and angry about everyone except for Rory. The two established a friendship, which aroused Dean's jealousy. Lorelai did not approve of their friendly relationship and marked Jess as having a negative impact on Rory, especially when they had a car accident that led to a dispute with Luke. Richard announced that he had retired, but soon became bored and established his own insurance company. Christopher seems to live with him, and Lorelai decides to get back together with him. But at Suqi's wedding, Christopher learned that his recently separated fiancee was pregnant and decided to return to her, which broke Lorelai's heart. Meanwhile, Rory impulsively kissed Jess.

萊拉（Lorelai）接受了麥克斯的求婚，但在婚禮前不久意識到感覺不對，於是他們分手了。 她和蘇祺對在破舊的獨立旅舘開店感到興奮，但老闆拒絕出售。 蘇祺與當地農民傑克森訂婚。 路克十幾歲的侄子傑斯·梅利亞諾在他的照顧下生活。 傑斯對除了羅莉（Rory）之外的所有人都感到悶悶不樂和生氣。 兩人建立了友誼，引起了迪恩的嫉妒。 萊拉（Lorelai）不贊成他們的友好關係，將傑斯標記為對羅莉（Rory）的不良影響，尤其是當他們發生車禍並導致與路克發生爭執時。 李察宣佈他已經退休，但很快就感到無聊並成立了自己的保險公司。 克裡斯多夫似乎有他的生活在一起，萊拉（Lorelai）决定與他複合。 但在蘇祺的婚禮上，克裡斯多夫得知他最近分居的未婚妻懷孕了，决定回到她身邊，讓萊拉（Lorelai）傷心欲絕。 與此同時，羅莉（Rory）衝動地親吻了傑斯。