14.01: "Wheel of Misfortune"
Another summer has passed and Lenny has some bad news - he has divorced Jill. Homer, Lenny and Carl decide to cheer him up by taking him on a road trip. However, the plan doesn't succeed after the van breaks down and they are suck in the middle of nowhere.
14.02: "Career Daze V"
Bored on a Sunday afternoon, Homer, Barney, Lenny, Carl and Marge all decide to take a look at more career what-ifs. What if Homer was a famous chef, what if Carl was a dangerous criminal on death row, and what if Barney was the owner of the Duff company?
14.03: "The Treehouse Report"
Lenny's younger brother is upset when his treehouse is torn down by heavy wind. Homer, Barney, Lenny and Carl decide to team up and all re-build it for him. Meanwhile, Marge is beginning to feel lonely without Jill around anymore, and she feels depressed.
14.04: "Mother's Secret Lover"
Homer is shocked to discover that the real reason his mother left him may have been because she was cheating on Abe. However, he later finds an old diary in the attic, and Abe becomes determined to do whatever it takes to stop Homer from reading it.
14.05: "Last of the Summer Whining"
Everyone is beginning to get fed up with Lenny constantly moaning about his break-up with Jill in the previous summer. They become determined to find out what happened, and so Lenny decides to gather them all up and tell the story. A flashback ensues.
14.06: "Homer Goes Bananas"
Homer, realising that he will need more income from Teen FM to pay this month's rent, decides to get a part-time job selling fruits and vegetables around Springfield. However, it proves difficult after realises just how unhealthy everyone is these days.
14.07: "Teen TV"
Homer realises that Teen FM has advanced over the past few weeks and a new network - called "Teen TV" - is formed. However, he is shocked to discover that he is being fired, as the new manager wants only fresh, new people to work there from now.
14.08: "Lady and the Camp"
Marge decides to get a job taking charge of an all-girls camp. However, she later realises just how difficult it is to control the girls. She enlists the help of Homer. But things get taken too far and they all end up confronting a very dangerous grizzly bear.
14.09: "Camp of a Killer"
Inspired from Marge's camping job (14.08), everyone decides to go on a camping trip. Things get out of hand when Homer accidentally destroys the tents and all their equipment, and now, they all must work together to get back to their homes in Springfield.
14.10: "Becky Dies"
Christmas has arrived and the celebrations come to an end when Homer realises that his old girlfriend Becky has died from a heart attack. However, he is not sure whether to show his true feelings about the events now that he is back together with Marge.
14.11: "What Would Marge Bouvier Do?"
Marge finds herself becoming the center of attention of all teens in Springfield, after the word spreads that she is good at giving advice. However, she later realises that she has lost her "groove" and she is afraid of facing a large group of angry teenagers.
14.12: "As Bad as it Gets"
After a particularly bad day, Homer becomes depressed, and Marge is afraid that he may become sucidal. To keep his mind off it, she decides to take him on a vacation. However, the resort turns out to be a total nightmare and she worries more about Homer.
14.13: "Mother, Can You Spare a Crime?"
Barney is upset after he realises that his mother constantly shoplifts all the time. He threatens to turn her in himself if she continues to do it. However, he later realises that she has some sort of problem, and so with Homer's help, he attempts to sort it out.
14.14: "Nobody Nose the Trouble I've Seen"
Homer manages to get himself into a fight in Moe's Tavern and his nose gets broken. Determined to get it fixed, he decides to visit a doctor. However, he is beginning to have second thoughts and considers getting a new nose with plastic surgery.
14.15: "Duck in the Middle With You"
Homer decides to adopt a pet duck, and Marge and the others are beginning to get fed up with it constantly being around. However, they later realise that Homer has become attached to this duck, and they realise that it will be harder than they thought.
14.16: "Crush Hour"
Both of Homer's feet are unexpectantly crushed when he is taking a walk with Marge, and he is finding it difficult to cope without them. He contemplates getting a wheelchair. Marge rememembers the time she was in a wheelchair, in a semi clip show.
14.17: "The Sun That Got Away"
For the past few weeks, the sun hasn't been out at all in Springfield, and Homer and the others are beginning to get fed up with all the cold. They decide to book a vacation to Florida. However, Lenny and Carl don't want to risk another vacation together.
14.18: "In the Basement With Barney"
Homer is shocked when he realises that Barney has been living in his basement for a while as he has been kicked out of his house. Homer must keep Barney's stay a secret. However, it proves difficult, and so he attempts to find a new apartment for him.
14.19: "To Live and Die in Springfield"
Marge finally discovers the truth about Simon - he faked his own death to avoid a major tax problem. With the help of a very nervous Homer, she attempts to track him down and find out what really happened. They encounter many problems on the way.
14.20: "Beyond the Music"
Homer has finally completed a new song with his band. However, even he thinks that it is awful. He contemplates giving up his band and focusing more on his actual life. But he can't seem to confront the other members about it, and he begins to panic.
14.21: "Marge's Choice"
Marge has been back together with Homer for almost a year now and she wants to know if she is doing the right thing. That night, two dreams take place, showing what her life would be like if she never met Homer, and what it would be like if she stayed with him.
14.22: "Shut the Duck Up"
Homer's pet duck is maturing and waking everybody in the neighbourhood up with constant loud quacking. Homer must make a choice of whether to keep his duck or not, possibly risking his friendship and and making many neighbours extremely angry everyday.