1.01: “Smash & Burn” (Pilot)

Bart is packing up the last of his possessions and accidentally destroys Lucy's deceased father's valuable vase, which was worth over one thousand dollars. Just as he is about to tell her the truth, she surprises everyone by announcing she is pregnant. Meanwhile, Lisa suggests to Milhouse that they go on a relationship course in a mountain lodge so they don't run into the same problems as they did before.

1.02: “The Great House Detective”

When Bart and Lucy arrive at their new home in the suburbs, they are shocked to discover that it has many problems. There is no electricity or heat, as their accounts have not yet been processed. With no other option, they decide to stay in a nearby hotel for the night but neither of them get any sleep. Meanwhile, Milhouse and Lisa start the mountain lodge relationship course, but things get off to a shaky start.

1.03: “I Dream of Coffee”

After settling down in his new home, Bart decides to look into opening up his own coffeehouse but realises how expensive it will be to get things started. Until he can afford to follow his dream, he decides to search for a part-time job but ends up getting one at someone else's coffeehouse. Meanwhile, Milhouse and Lisa return from their relationship course as a brand new couple.

1.04: “Housewarming Barty”

Lucy encourages Bart to invite some of the neighbors over for a housewarming party but things get off to a shaky start when it is mistaken to be a college party. Bart and Lucy must find a way of getting everyone out but end up resorting to violence, causing them to get in trouble with the police. Meanwhile, Lisa manages to convince Milhouse to start searching for a house in the suburbs as well.

1.05: “Jailhouse Jitters”

Bart must work the night shift at the coffeehouse, and finds himself drinking a lot of coffee to help him stay awake. He ends up getting addicted but realises he will have to hide this from Lucy. This proves difficult when he is accused by a police officer for taking illegal drugs and is thrown in prison. Meanwhile, Milhouse and Lisa begin to house hunt and they consider purchasing a house down Bart and Lucy's street.

1.06: “Marge and in Charge”

Marge is coming to visit, and Bart is afraid that she won't approve of his new lifestyle, especially since he now works with minimum wage at a nearby coffeehouse. With the help of Lucy, he tries to come up with a big act to show that he is successful. Meanwhile, Milhouse is stuck babysitting Becky and James and he is afraid that Lisa will make house hunting decisions without him.

1.07: “The Thanksgiving Story”

Thanksgiving is approaching, and Bart invites Milhouse, Lisa, Tom and Jake for dinner at their house. Milhouse and Lisa surprise everyone by saying they are moving to the neighborhood and Bart doesn't know how to deal with this news. Lisa realises that she never got to know Lucy very much and they decide to bond. However, it turns into a disaster when they realise that they have nothing in common.

1.08: “Wheel of Misfortune”

Bart decides that it is time he purchased a car, but realises that he is being taken advantage of by all salesmen. Lucy accompanies him to a used car lot and they decide to just buy one. However, they later regret making this decision when it won't even move. Bart is late for work and Lucy must get home to finish cooking a romantic dinner. Meanwhile, Lisa and Milhouse's offer for the house is accepted.

1.09: “Bad Noise”

Lisa and Milhouse prepare to move down Shrub Street but have doubts when they discover how rowdy their neighbors can get when it comes to the New Year. All this aside, Milhouse convinces Lisa to ignore the rumors, but later regrets making this decision when they find themselves lying awake during their first night in, resulting from some very loud music. Meanwhile, Lucy forbids Bart from attending a party.

1.10: “Dude Ranch Daze”

To celebrate Lisa and Milhouse arriving in Shrubsville, Bart and Lucy invite them to a dude ranch owned by Lucy's grandfather. Bart and Milhouse spend most of their time together but end up wreaking havoc, resulting in them in working against their will at the ranch. Meanwhile, Lisa and Lucy decide to go horse-riding together but they end up getting lost in the forest and must work together to get out safely.

1.11: “There's Something about Bobby”

Bart and Lucy introduce themselves to a new neighbor named Bobby Falcon and they are shocked to discover that he is a millionaire looking for a quite lifestyle. Lucy tries to befriend him but Bart takes this the wrong way, thinking that she finds him attractive. Meanwhile, Lisa begins searching for a job but realises she and Milhouse must first find a babysitter. However, nobody suits the qualifications.

1.12: “The Old Van and the Key”

After coming across an old van in the dumpster, Bart and Lucy decide to go on a road trip but things end up getting ruined when Lucy's pregnancy constantly gets in the way. Depressed, they turn around and head back home but they lighten up after Lucy discovers that she will be having a baby boy. Meanwhile, Lisa considers following her other childhood dream of becoming a chef. Hilarity ensues.

1.13: “People's Will Talk”

Bart is deeply affected when he discovers that his old friend Eddie from New York has recently died in a car crash. Before he travels to the funeral, he is convinced he should write his own will "just in case", resulting in a fear of death. Meanwhile, Lisa gets a job interview at a fancy restaurant on the outskirts of Shrubsville but realises she must make a tough choice after finding out the hours involved.