2.01: Back Together
Maggie and Gerald are back together, and Marge is not too happy about this. She attempts to introduce her to another guy before she gets serious with Gerald, but she soon realises just how difficult she is to convince that Gerald is not the right guy for her and are stuck on what to do.
2.02: Halloween Pranks
When Maggie discovers that Gerald has many pranks planned for Halloween, she attempts to convince him not to go through with anything. But when he fears that she may break up with him for being too immature, he decides to change his personality for good, but soon begins to find it difficult.
2.03: Fast Food
Maggie believes that she is getting slightly overweight, and so she becomes determined to go on a diet. After realising just how difficult it is, she, along with Gerald, Arnie and Rachel, attempt to go on a campaign to get fast food banned from everywhere in Springfield, but the mayor is hard to convince.
2.04: Drinking Problem
Arnie starts to frequently visit the new bar in Springfield, and Maggie and Rachel begin to believe that he has a drinking problem. The two team up to get Arnie back to normal, unaware that Moe has his own plans up his sleeve to destroy the new bar's business once and for all!
2.05: Maggie's Crisis
Maggie believes that she has been allowing a guy at Springfield High to flirt with her, and she believes that getting into a serious relationship with Gerald could not be a good idea, and so she must choose between the two. When they find out, they try all they can to win her affection.
2.06: The New Era
It is time for the new year at Springfield High, and Maggie is not happy about her new schedule. She attempts to change it, but it ends up getting mixed up with someone else's and she is forced to take many strange classes, and what's worse is that the principal is not convinced that she is telling the truth.
2.07: The Break
Still with Gerald, Maggie recommends that they speak to a relationship counselor about their problem. The two agree to take a break from eachother, but they can't help still having large feelings for eachother, and they find it difficult to maintain a break and must decide on what to do.
2.08: Springfield Dating Game
Rachel is asked to appear on a Springfield public access show called The Springfield Dating Game, and her ending result is a total nightmare. When she discovers this guy could be related to none other than Gerald, she attempts to find out why the two are so different, but it is difficult to do so.
2.09: Maggie's Job
Maggie agrees that it is her turn to pay for a date with Gerald, but she soon realises that she has no money! Desperate for some cash, she gets a job at a newspaper. She begins to suspect that her boss, Andrew, doesn't recognise her writing skills and all he is interested in is coffee. She attempts to prove this.
2.10: Gerald's Family
Maggie reveals to the Simpsons that she is spending the holidays with Gerald and his family. They are incredibly shocked, and so they become determined to do whatever it takes to get her to re-consider. But, this is difficult, and Maggie ends up hating Gerald's family, and wishing that she was with her's.
2.11: The Article
When Maggie is asked to write an article for the Springfield Shopper, she has a happy moment with Pete and she ends up sharing a passionate kiss with him. This makes her feel guilty because of her boyfriend Gerald, and she must decide onthe two, putting herself behind on the article.
2.12: Uncofortable Job
Pete and Gerald are both trying all they can to win Maggie's affection, but Maggie decides on Gerald in the end. When she starts to feel uncomfortable working around Pete at the Springfield Shopper, she considers quitting, but Gerald attempts to convince her to stay as it is her perfect job.
2.13: The Dance
The annual Springfield High second year dance is coming up soon, and caught up in the excitement, Maggie agrees to go with Pete. Now, she must find a way to tell Gerald without him getting angry, but this is impossible. Stuck on what to do, she has no choice but to go with both of them at the same time.
Maggie, believing that she doesn't receive enough pay from the Springfield Shopper, decides to start a babysitting service. She ends up being asked to babysit Gerald's baby brother, and he turns out to be a total nightmare. When she accidentally flips and hits him gently on the head, she must conceal the bump.
2.15: Rachel's Brother (1)
Rachel's brother, Tim, shows up at Springfield High, explaining that he has been transfered there because of a problem back home with their parents. Rachel becomes determined to find out what the problem is, whilst the others are more concered about how misbehaved this brother really is.
2.16: Family Problem (2)
Rachel discovers that her mother and father are splitting up, and she feels incredibly upset. She is even more upset when nobody comforts her, as they are all too worried about Tim. Feeling alone, Rachel depends on Tim to help her feel better in a brother/sister moment, but her hopes are soon shattered.
2.17: Pizza Delivery Girl
A pizza is delivered to Maggie at the Simpsons house, and it turns out that the delivery girl was Gerald's ex-girlfriend. The two become good friends and start talking about Gerald, but Maggie soon fears that this girl is only interested in getting him back for herself, and they end up becoming enemies.
2.18: Punching Gerald
After a date, Maggie gets angry at Gerald and she accidentally punches him. She attempts to find a way to make it up to him, but she soon realises just how embarassed he is after being punched by a girl, and so she must find a way to remove his embarassment before it is too late.
2.19: Arnie's Dad
Arnie has a shock when a man turns up at Springfield High, explaining that he is is father. With the help of Maggie and Rachel, the three try to find a way to see if this guy is really his father, but Arnie attempts to put an end to the tests when he becomes good friends with him.
2.20: Football Game
After getting into a fight with Rachel and Maggie, Arnie and Gerald challenge them to a football game. Everything begins to go over the top and Gerald and Maggie get extremely mad and decide to take a break from eachother. Arnie can't help feeling responsible.
2.21: Fake Relationship
Maggie discovers that Gerald has found a new girlfriend already, who is called Suzie (1.17 New Girlfriend). Angry at him, Maggie becomes determined to make him jealous by hiring a guy to pretend to be her new boyfriend, but the ending results are terrible.
2.22: Summer Days
The second year of Springfield High has ended, and so Maggie, along with Arnie and Rachel, decide to take jobs at a summer beach resort in a not too distant town. They soon realise the trials and tribulations they will be going through this summer.