2.01: “Bart Goes Hawaiian”
Bart and Lucy decide to go to their favorite vacationing place Hawaii to spend some romantic time together before the baby boy is born. However, they are infuriated when they discover that Milhouse and Lisa have decided to tag along. Desperate for some time alone, they make a break for it but later regret doing so. Milhouse must calm down Lisa who is worried about James and Becky.
2.02: “Bobby Doesn’t Live Here Anymore”
Bart and Lucy’s rich neighbor Bobby Falcon is planning to move once again and it’s not long before the house is sold. Lucy decides to invite their new neighbors over but is infuriated at how messy they are. She hassles Bart to do something about it. Meanwhile, Milhouse discovers that Lisa has a crush on Bobby Falcon and he can’t help feeling jealous, and he becomes desperate to “beat him”.
2.03: “The Kid Stays Out the Picture”
The day of the baby boy’s birth is drawing ever closer, and Lucy is afraid after hearing what labour can be like. She turns to Bart for comfort, but she realises that he doesn’t seem interested and is scared that he isn’t suitable to be a father. Meanwhile, Becky’s eighth birthday is on the horizon and Milhouse is left in charge of the preparations when Lisa must work late. He realises he can’t deal with the pressure.
2.04: “Herb’s Hideaway”
Bart, Lucy, Lisa and Milhouse are all invited to Herb Powell’s holiday home in the south of France. Marge is also there, and she is shocked when she realises that Herb is trying to seduce her, making her think she is not over the deceased Homer yet. Bart is having trouble enjoying himself when Lucy’s pregnancy is once again getting in the way, and Milhouse encourages Lisa to help him search for the supposed hidden treasure.
2.05: “Where No Tan Has Gone Before”
Milhouse becomes inspired to get a spray-on tan after realising that it is very popular in Shrubsville nowadays. Lisa tries to convince him that it is not a good idea but he doesn’t pay attention. He later regrets not listening to her when it goes horribly wrong and he gets four layers of spray-on tan all over his body. Meanwhile, Lucy is shocked to discover that the baby’s birth is late, and she and Bart go to the doctor.
2.06: “Someone like Jew”
When Milhouse finds some of his old things in the attic, he later discovers that he may have a Jewish heritage and decides to find out more about his culture. Lisa fears that he may take things too far. Meanwhile, the doctor recommends Bart and Lucy have sex to speed up the process but they seem nervous around each other. Just as they are about to try it, she goes into labour and is taken to the hospital.
2.07: “Insane in the Medicine Game” (1)
Bart has taken Lucy, who is now in labour, to the hospital and she is taken care of immediately. However, she becomes nervous when she realises that all the available doctors have some very strange flaws. Bart becomes determined to find the right doctor before it is time for their baby to be born. Things turn for the worse when he begins rushing around the hospital menacingly and crashes his head.
2.08: “Insane in the Medicine Game” (2)
Bart finds himself in a hospital bed, unable to move. He must get to the delivery room before Lucy gives birth, but it proves nearly impossible. Lucy has trouble dealing with the fact that she may have to give birth without her husband by her side and patronising doctors don’t exactly help her out in this crisis. Meanwhile, Milhouse and Lisa have no choice but to take Becky and James to the hospital with them.
2.09: “Cry another Day”
Bart and Lucy have recently returned home from the hospital, with their new baby boy Dennis. They have trouble dealing with his constant crying and realise they have no choice but to bring back an ex-babysitter, who is an expert in getting babies to stop crying. Meanwhile, Milhouse and Lisa discover that Becky has a bullying problem at school, but realise that she’s the one who is actually the bully.
2.10: “Crush Hour”
Milhouse decides to prove to Lisa that he can be tough by entering the upcoming Shrubsville marathon. Everything seems to be going fine until a large pile of debris falls on him and he gets his leg crushed, confining him to a wheelchair. Determined to show that he can still be tough, he decides to enter the upcoming wheelchair races instead. Meanwhile, Lucy is afraid that she is needed back at work already.
2.11: “Bart’s Mom has got it Goin’ On”
Marge invites Bart, Lisa, Lucy and Milhouse for Thanksgiving dinner and surprises everyone by announcing that her new boyfriend is Herb. Bart has trouble dealing with this and with the anniversary of Homer’s death coming up on the horizon, he just can’t cope. Meanwhile, Milhouse enjoys being in Springfield once again but manages to get too excited and is thrown in prison by some incompetent police officers.
2.12: “Meat Lisa Simpson”
Lisa is excited when she gets a promotion at the restaurant but later realises that her new job involves cutting up a lot of meat. She must make a decision – her career or her vegetarianism. However, it proves a very tough choice. Meanwhile, Bart’s job at the coffeehouse is under threat when he seems to be spending most of his time with baby Dennis. He must win back his boss’s respect to keep the money coming in.
2.13: “Coffee Hallucinations”
Bart is asked to start serving a new brand of coffee at the Shrubsville coffeehouse but is shocked to discover that it is causing many people to have strange hallucinations. His boss is arrested and is accused of slipping illegal drugs into the coffee batches and Bart realises his job may be under threat once again. He is even more shocked when he realises that it may have all been caused by one of his own mistakes.
2.14: “Whatever Happened to Baby Dennis?”
Desperate for a babysitter, Bart must resort to Marge and her new boyfriend Herb. He is still uncomfortable with the fact that they are together and when Dennis turns out missing at the end of the day, he immediately blames Herb. Meanwhile, Lisa is shocked to discover that some of the most popular meals has been taken off the restaurant menu and has been replaced with store-bought items instead.
2.15: “Married Away”
Bart is shocked when he discovers that Lucy was briefly married to someone when she was nineteen years old. She explains that it was a pity marriage, and not one for the correct reasons. Bart feels uncomfortable with this but decides to let it pass. However, it proves difficult when her ex-husband shows up explaining that he needs somewhere to stay. Meanwhile, Marge tells Lisa she is going to be marrying Herb.
2.16: “Take Me Out to the Brawl Game”
Desperate for some extra income, Bart decides to gather up some of his neighbors and form a baseball team and enter them in an upcoming tournament. However, he later regrets making this decision after realising that Milhouse is doing the same thing, possibly causing a rift between them. Meanwhile, Lisa discovers that Becky and James feel competitive against the newly-born baby Dennis.
2.17: “The Herb Who Came to Dinner”
Bart invites Marge and Herb over for dinner to discuss wedding arrangements. However, Herb is more interested in holding the wedding ceremony as fast as possible, making Bart suspect something. With the help of Lisa, he tries to find out what is going on. Meanwhile, Milhouse spends the afternoon babysitting James, Becky and Dennis so Lucy can have some time alone. He later regrets asking to help.
2.18: “Chicken Pox Run”
When James comes down with a case of the chicken pox, Bart and Lucy are afraid that Dennis may get it as well. Lisa realises that Becky never had the chicken pox so she sends her into “quarantine” with Milhouse, who has never had it either. Milhouse has trouble passing the time with Becky and the scratching makes things worse. Bart and Lucy become extremely overprotective of Dennis.
2.19: “You Don’t Know Crack”
Bart discovers that some of his co-workers at the coffeehouse do drugs and he is afraid that they will trick him into doing the same. He tells Lucy about this, who blabs everything to the boss. The boss sends them all to re-hab, including Bart who proves to be very unpopular with everyone else. Meanwhile, when Dennis gets his first glimpse of violence on television, Lucy is afraid that it may have affected him.
2.20: “Lisa and Milhouse Host Sunday School”
Lisa decides it’s time Becky and James went to Sunday school so they can eventually make their own decisions about religion, but she later realises that there is no teacher to teach them. She manages to convince Milhouse to apply for the job with her, but they both realise how bad they are with a large group of children. Meanwhile, Bart decides to quit the coffeehouse after getting fed up with his co-workers.
2.21: “Adoption Day”
Milhouse accidentally lets it slip in a form that James was never adopted. He then receives a phone call explaining that James could be put in a foster home any day now. Milhouse must get James adopted properly before that day comes, but finds it hard without having to tell Lisa. Meanwhile, Lucy begins hassling Bart to find a job elsewhere after recently quitting the Shrubsville coffeehouse.
2.22: “The Wrench Connection”
Bart, desperate for income, applies to be a mechanic but realises he must prove that he is suitable for the job. Desperate for anything, he decides to sign up for the annual Shrubsville “fix-it” competition. He later regrets making this decision after realising what kind of people he will be up against. Meanwhile, Lisa is infuriated that Milhouse didn’t tell her about the adopting James crisis.
2.23: “A Facelift in the Crowd”
When Lisa and Milhouse run into one of Lisa’s ex-boyfriend during a day out at the zoo, Milhouse is afraid that she still finds him attractive. Desperate for her affection, he considers getting a facelift. When Bart manages to let things slip, she becomes determined not to let him do anything stupid. Meanwhile, Bart considers getting a job as a male model but is afraid when he realises he may have to pose nude.
2.24: “Clothes Doors”
Lucy decides that it is time she looked for a more high-paying job. She is excited when she is offered a job as a fashion designer, but when her old boss finds out, she is fired. Things turn for the worse when she is told she will be designing male clothes and finds it difficult not to make anything too feminine. Meanwhile, Bart looks into finding a suitable preschool for Dennis for when he is a little older.
2.25: “Marge and Herb’s Wedding”
The day of Marge and Herb’s wedding has finally arrived, and Bart is still feeling uncomfortable. He gets into a panic and manages to fall onto the floor, where he experiences a hallucination. In his hallucination, the deceased Homer explains that everything will be fine. Bart wakes up, feeling better, but soon discovers that Herb is nowhere to be seen, and a large part of Marge’s bank account is missing…