5.01: “Marry Me a Little”

Bart and Lucy decide it is time they re-newed their wedding vows, but Bart feels guilty for moving out of the Simpsons home. And when he discovers there are promotion possibilities at the Shrubsville times newspaper, he must make some harsh decisions about his life. Meanwhile, Lisa is outraged when she discovers Milhouse has been teaching James how to play some annoying pranks on people.

5.02: “Motel de Love”

As Malcolm’s fourteenth birthday approaches, Milhouse and Lisa prepare to visit him in New York. They are shocked to discover that he has been living in a crummy motel with Amy ever since she divorced her husband. Lisa is infuriated when Milhouse asks them to move in, without her permission. Meanwhile, Bart has trouble telling his boss at the newspaper that he is quitting his job to become a journalism tutor.

5.03: “Airplane and Simple”

Bart realises it is hard being a journalism tutor when you don’t work at a university, and decides to go on a vacation with Lucy to keep his mind calm. However, they end up boarding the wrong airplane and arrive in England. There, Bart is excited by all the journalism oppurtinities available, but Lucy just wants to get home to Dennis. Meanwhile, Malcolm and Amy prepare to move in with Milhouse and Lisa.

5.04: “Fools Crush In”

Amy has moved in, along with Malcolm, and Lisa is angry when she starts to disrupt their private lives. Malcolm enjoys spending a lot of time with Maggie at her house on the other side of Shrubsville and she freaks out when she realises that he is developing a crush on her. Meanwhile, Bart looks into becoming a journalism tutor at Shrubsville University, but begins to miss his old job at the newspaper.

5.05: “World Turned Upside Down”

Milhouse is shocked when he realises Amy has started to flirt with him, and without knowing what to do, he orders her out of the house. However, he must face an upset Malcolm before doing so, as he doesn’t want to say goodbye to his mother once again. Milhouse’s world is turned upside down when Amy tells him she is still in love with him. Meanwhile, Bart has trouble with his new journalism student at the university.

5.06: “Emotional Rescue” (1)

Milhouse is having difficulty coming to terms with his true feelings and decides to go on vacation by himself. However, he realises he has booked himself into a woman’s retreat and the only way of leaving is to pass a special course, because, as a man, he is considered a sexist pig and must get in touch with his feminine side. Meanwhile, Lisa is convinced she is the one to blame for Milhouse vacationing by himself.

5.07: “Emotional Rescue” (2)

Milhouse has completed the feminist course at the woman’s retreat and returns home. He discovers Lisa is repulsed by his new personality, where as Amy finds it attractive. With the help of Bart, he attempts to become masculine again, however Amy constantly gets in his way. Just as Milhouse is about to complete Bart’s special training program, Lisa discovers the truth about how Amy feels about Milhouse.

5.08: “The Brawl Game”

Milhouse and Amy must work out living arrangements for Malcolm, but it seems that five minutes of quiet discussion can’t pass by without it turning into a large brawl between the two of them. Malcolm turns for Maggie for advice about his life. Milhouse wakes up next to Amy and is afraid he slept with her, and must come to terms with what he has done. However, things turn for the worse when he catches her with a pregnancy test.

5.09: “The Honeymoon’s Over”

Bart suggests to Milhouse that he takes Lisa on a second honeymoon to keep his mind off the whole Amy fiasco. Milhouse takes up this idea and books a vacation to Hawaii. However, everything turns into a nightmare when they discover their suite has been given to none other than Bobby Falcon, who is now richer than ever. Meanwhile, Bart is afraid he finds one of his journalism students attractive.

5.10: “Dennis the Tennis”

Bart and Lucy decide to spend the day at the Shrubsville sports club. With no babysitters available, they are forced to take Dennis. Bart doesn’t seem to enjoy himself, but later discovers that Dennis plays tennis extremely well. Lucy is proud of him but she assumes that Bart wants to take advantage of Dennis’ tennis skills, and she is infuriated. Meanwhile, Milhouse can’t keep his mind off the Amy disaster.

5.11: “Like Hike”

Maggie is enjoying spending time with Malcolm and she discovers that he enjoys hiking. After noticing that he is pretty much being rejected by his parents, she decides to take him hiking. However, she later regrets making this promise after hearing the dangers of hiking, especially with a young teenager. Meanwhile, Milhouse and Lisa return from their second honeymoon and Milhouse feels he can’t hide it any longer.

5.12: “Chemical Reaction” In the landmark one-hundredth episode, Milhouse prepares to tell Lisa what he did. However, a manipulative Amy doesn’t exactly help him out in his nervous situation. Lisa reacts to the news in many different ways and finally decides on kicking him out of the house. Amy starts to see the light and decides to patch things up between the two. However, Milhouse takes this the wrong way and thinks she is up to no good again.

5.13: “Picture Perfect”

Lucy decides it is time a family photograph was taken. However, Bart realises he is no longer able to smile on camera, and decides that it has been that way ever since he attended Homer’s funeral. Lucy attempts to get him to smiler, but alas, nothing works. She decides to cheer him up by taking him to visit Homer’s grave in Springfield but he takes this news badly. Meanwhile, Amy moves out and Malcolm stays.

5.14: “Moaner Lisa Smile”

Lisa tells Milhouse she is willing to forgive him in time. However, after days of thinking she realises that she can’t even look at him anymore. Milhouse returns home from work and discovers a divorce paper lying on the table. Heartbroken, he signs it, for her. He prepares to pack his bags but realises that Lisa has already done so herself – and moved to Springfield with Marge. Malcolm comforts him as tears run down his face.

5.15: “Bart on the Range”

Lucy’s parents invite her and Bart to their cattle ranch in the deep south. Lucy is angry when Bart explains he can’t go but then forgives him when she realises that he is staying for Milhouse. However, Milhouse doesn’t want him to stay out of pity and decides to tag along. Lucy is shocked when the subject of another child comes up from her mother. Milhouse wallows in self-pity and Bart attempts to cheer him up.

5.16: “The Ex Who Almost Came to Dinner”

Milhouse is shocked when he realises that he has been invited, along with Bar, to dinner with Marge and Herb in Springfield. He refuses to go but later realises that it was Lisa who sent the invitation. He hopes that she may have had a change of heart, but when she calls to cancel, his hopes are immediatley shattered. Meanwhile, Maggie decides to take Malcolm to New York so he can visit Amy but realises she will have to do it in secret.

5.17: “Love, Van Houten Style”

Becky has a crush on the most popular boy in Shrubsville Elementary, Rick West. However, she doesn’t know how to catch his attention and turns to Malcolm for some “big brother” advice. The two end up becoming close in the process and Malcolm subconsciously begins to think that she has a crush on him. He attempts to keep his mind of this but ends up sabotaging Rick and Becky’s possible relationship in the process.

5.18: “Promotion Commotion”

Bart is excited when there is a possible promotion in sight. However, he realises that this was nothing but a rumor and in fact, people are being fired all round the journalism department at Shrubsville University. He becomes determined to find out whether he is among the people who will be fired, which proves tougher than he thought. Meanwhile, Milhouse is depressed when Lisa calls about seeing Becky and James.

5.19: “One Foot in the Wave”

Bart is shocked to discover that a rumor is spreading round the town that a huge wave is heading for Shrubsville, and this is the time of year for surfers to come from all over the world to ride the high waves. He considers entering a surfing contest after another surfer flirts with Lucy on the beach. Meanwhile, Lucy decides to spend her time doing something worthwhile and teach Dennis how to swim. However, this proves difficult.

5.20: “I Re-Married Marge”

Bart is shocked when he discovers that Marge and Herb have taken themselves off to Las Vegas to re-new their wedding vows. However, Bart realises that there is something else going on and confronts Herb about it – their previous marriage wasn’t legal. Herb gives in and explains that he got his friend to perform the fake ceremony as he was in debt to a Vegas casino. Meanwhile, Lucy decides to hit the slots.

5.21: “Pregnancy Pandamonium”

Malcolm is alone in his house and is shocked when Amy turns up, demanding to see Milhouse. She refuses to leave until he comes home from work. Not wanting his dad to get upset again, Malcolm attempts to get her to leave but ends up calling the police on her. However, he feels guilty when she explains that she is pregnant. Meanwhile, Bart realises that he has made an expensive blunder at work.

5.22: “Rockumentary”

After causing an expensive blunder at Shrubsville University, Bart is demoted to be a journalist for the university newspaper. He attempts to cause some fuss but ends up regretting doing so after the job of interviewing a famous rock band is given to someone else. Determined to get involved, he tries to get on his boss’ good side again but ends up making things worse. Meanwhile, Milhouse discusses Amy’s pregnancy.

5.23: “Degenerate Heart”

Milhouse has started to feel depressed what with his divorce soon being final and his ex-girlfriend’s pregnancy. Bart and Lucy decide to cheer him up by throwing a party for him but he ends up collapsing on the floor, suffering from a heart attack. After being taken to the hospital, the doctor explains that it resulted from pure stress. Afraid that Milhouse will have another one, Bart has no choice but to phone Lisa and ask for help.

5.24: “Ash Course”

Lucy asks Bart to clear out the attic to make way for some old furniture. He climbs up and discovers two urns. Bart becomes determined to find out about the history of the house so he can give a proper send-off to the people inside the urns. However, he later discovers that the history of the house is a lot more tangled than he thought. Meanwhile, Amy visits Milhouse in hospital and shocks him by saying he can be involved in parenting.

5.25: “The Second Coming of Lisa”

Lisa returns to Shrubsville to visit Milhouse in the hospital. However, she is infuriated when she discovers Amy by her side and runs off back to the bus station. Milhouse, determined to get everything back to normal, attempts to chase after her and explain everything. Bart attempts to stop him from doing anything stupid. Just as Milhouse catches Lisa’s attention, she is run over by a truck. Milhouse and Bart stand there in shock…