Luke makes a bigger fuss than Davey when Sookie and Jackson bring their son into the diner; all of Stars Hollow is amused when Taylor returns from his Caribbean cruise with a drastic change in his appearance; Richard and Emily are stunned when Floyd informs them that Lorelai and Jason have been dating for months; Luke comes to the rescue when Kirk's failure to make a map of the Easter eggs he hid in the town square gets Taylor's nose out of joint; Richard and Jason discover that Floyd's peacemaking overtures are a disguise for his plan to ruin Richard financially by suing them for stealing his clients; while shopping with Lane in Doose's, Rory has harsh words about Lindsay as she relates her quarrel with Dean over his plans to drop out of college to earn more money to buy a house, unaware that his wife is listening in the next aisle; Richard resolves his problems with Floyd at Jason's expense; Dean and Rory agree to continue their friendship despite Lindsay's demand that they stop spea

T.J. is milking his injuries for all he's worth, but Luke decides that it's time to go home after seven weeks on the Ren Faire circuit; Rory calls to apologize and to ask her mother to deliver a letter to Dean; Sookie accurately diagnoses Lorelai with a bad case of management burnout, and the two friends decide to decompress with a girls-day-out; Emily and Rory come home exhausted from fending off the attentions of randy European men; Michel is wildly unenthusiastic when he's pressed into babysitting for guests whose children take an inexplicable shine to him; after Lindsay finds Rory's letter, she throws Dean and all his possessions out of the house, and her mother has an angry confrontation with Lorelai in the town square; Lane realizes that she's falling for Zack; Rory is saddened when Dean expresses regret for the shift in their relationship and the harm it caused to his wife and their families.

Lorelai does her best to get Luke to not give up on them after the awful events at the wedding. Luke tells her he needs some time and Lorelai can't take it. Rory asks Logan to hang out with her but is upset that when she gets to his place that there are a lot of people there. She gets a call from Sookie who tells her that Lorelai is in bad shape after Luke told her that he didn't think he could be in this relationship. Rory doesn't have a car, but Logan lets her borrow his car and driver. Taylor has the whole town taking sides for either Luke or Lorelai. After taking care of her mom Rory goes back to Yale to work things out with Logan, making sure he understood that the hanging out didn't just mean hanging out, it meant alone time.

Feeling a little lonely, Lorelai adopts a dog. Luke agrees to repair Lorelai's house, rather than buy the Twykham house. This soon turns into trouble as TJ does some unwanted construction on the house. Rory starts her community service assignment. Feeling neglected and unhappy with how things are going, Rory visits Luke at his diner. He lets it slip that he and Lorelai are engaged, leaving Rory feeling even more alone.

As Valentine's Day approaches, Rory and Logan invite Lorelai and Luke to spend a weekend with them at Logan's family's house on Martha's Vineyard. Lorelai is upset by Luke's unfriendly attitude toward Logan. Luke's attitude changes when he realizes he forgot to buy Lorelai a Valentine gift, and Logan saves the day. When Lorelai finally confesses to Luke that she is worried the wedding will never take place, he reassures her that they will get married soon. The weekend ends in an ugly scene when Logan's father, Mitchum Huntzberger arrives.

Although Rory and Logan are back together, Logan is miserable knowing that Rory hasn't really forgiven him, and he takes off with his friends for another stunt with the Life and Death Brigade. Rory accepts Jess's invitation to attend an open house at his new book store/art gallery/publishing house in Philadelphia. While there, she is surprised to run into Luke, who is accompanying his daughter April on an academic field trip.