Soon after Jamie was born and after the disaster day care at the church, Lois and Hal hired a babysitter for him, Polly. She started babysitting him in the episode Watching The Baby. Polly was seen leaving the house, assuring Hal that she could stay for longer if she wanted to because of Lois being too tired to take care of him on her own, but Hal insisted she leaves. When she found out what day it was, she remembered she had a court case, where she was filing a restraining order against her sister for stealing her boyfriend of whom she was his first and third wife. Malcolm, Stevie, and Reese were seen criticizing her and revealed that she was a well-known weirdo in the neighborhood who had earned many nicknames for her bizarre endeavors. She is known as "The Cat Lady" and "The Naked Jogger", implying that she's done things like this in the past.
She appeared again in the episode Malcolm's Job, where she was teaching a "Daddy and child" class. Lois made Hal and Jamie go to the class with her. She started giving the dads a spiritual yoga class, where they moved their babies limbs into yoga positions which matched hers. Hal and the other father kept returning to the class, willingly because while she was gone, they did a bunch of random contests with their babies, such as stroller races and full diaper weighing.
In the episode Hot Tub, Polly was babysitting Jamie again and wanted a ride to the Lucky Aide. Malcolm, having recently gotten his learner's permit, willingly drove her there. Things eventually got wildly out of hand because on the way there, she had him stop by her ex-boyfriend's house, where she stole an urn filled with the ashes of her mother and got Malcolm to keep it a secret and go along with taking it back to her house. Malcolm was later confronted by Danny, himself, who was angry at him. It was then explained that Danny father, Polly's cat, and a dog that belonged to both of them was also in there. While they were dating, they thought their relationship would last forever so they mixed their family's ashes the way they would with CDs or dishes. Malcolm freaked out and started driving the car again, taking Polly with him. She had the plan to hide the ashes and herself at The Wilkerson House, so that he wouldn't find them. Unfortunately, Danny was in the car the whole time. The two of them got into a huge fight, which made Malcolm crack under the nerve-wracking pressure and dump all the ashes into the wind. Polly and Danny eventually calmed down and made up, and came to common grounds on why their relationship had to end. Fortunately for them, Lois and Hal were at the hospital and didn't get home until after they did, so they got off scot-free with it.
In the episode Polly in the Middle, Abe fell in love with her and wanted her to fill in for the empty void where his ex-wife, Kitty Kenarban used to be. Hal set her up on a date with Abe. The two of them started dating each other and they both felt a whole lot happier. On their third date, Polly was getting ready for another date. However, the person who she took on this third date was not Abe, but Craig Feldspar. It turns out Lois had set him up on a date with Craig, with her relationship with Craig being unbeknownst to her. Polly said that she could not make a decision because she loved them both for so many reasons and continued having an affair with them, and even implied that she wanted to have a polyamory with them. One time, Abe and Craig both met Polly in the same place at the same time and found out the truth, leading to an extremely dramatic sissy fight between the two of them. Polly had finally made up her mind and chosen that she'd rather not date either of them because she was devoting too much of her life to her relationship that she could have been devoting to her babysitting career.
At some point, Polly must have stopped babysitting Jamie because she had stopped appearing, probably her crazy behavior became too much for them. In the episode Malcolm Defends Reese, she was replaced by a lady named Claire.
- Jamie Wilkerson - Polly considers Jamie to be a friend of hers because she always babysits him and spends a lot of her time taking care of him. With her hippie personality, she believes that she connects with him on a spiritual level and can understand his emotions and how he feels around her. She understands that he likes it when she's around and likes how much fun they have together and approves for their relationship together as a friendship. In the episode Polly in the Middle, she even claimed that her interaction with Jamie is more than just a friendship, but also an important part of her life. Even more important than a romantic relationship because she really needs to nurture and care for Jamie and make him grow up to be a happy and successful person.
- Malcolm Wilkerson - In the episode Hot Tub, Polly and Malcolm had developed a somewhat friendly interaction. Before, Malcolm sort of looked down upon Polly for being weird and bizarre, and Polly thought nothing of Malcolm. Due to this episode's events, they were brought closer together. Malcolm had just gotten his learner's permit and became obsessed with driving, so when Polly needed to be driven somewhere, he willingly took her along. It turned out Polly was stealing the ashes of dead relatives of hers from her ex-boyfriend. Malcolm started thinking that she was completely insane for doing this and was hesitant to help her. However, Polly's ex terrified him so much, that he had no choice but to help her and since their endeavor ended with them getting off scot free, Malcolm and Polly became happy with each other's presences and just sort of became friends.
- Lois and Hal Wilkerson - Polly must be friends with Hal and Lois because they hired her to babysit Jamie. However, they probably only hired her because she would take Jamie off of their hands, because they expressed a lot of slight for her in the episode Malcolm's Job, where she had a "Baby Yoga Class" that she asked them to come to and the two of them argued over who had to go, both wanting the other to go. Lois won the argument and Hal had to sit through her lessons, much to his discontent. In the episode Watching The Baby, Polly was wanting to stay and babysit Jamie for a little while longer, while Hal pushed her out the door, annoyed with her talking and was relieved to be free of her when she was gone.
Polly has a ton of extremely severe problems with her entire family. Most of these problems are so big, that they involve legality issues. None of her family members are ever seen, but they are mentioned by her in conversation.
- Mother - In the episode Hot Tub, it was revealed that Polly's mother had died and she put her ashes in an urn, along with the remains of her cat, boyfriend's father, and a dog that belonged to both of them. Her mother's cadaver must have also been lying around the house for a long time before she cremated it, due to information she would later explain about her fathers. (see "Fathers" below)
- Fathers - In the episode Malcolm's Job, Polly mentioned that she had to make a call to a parole officer about "one of her dads". This implies that she has two dads and one of them is causing her a lot of problems that involve the law. She also mentioned that her fathers gave her "daddy issues" which led her to sleep with a ton of men in college. In "Hot Tub", she mentioned her biological mother being dead. So, it's possible that her biological father was bisexual and remarried a man. This must have been while she lived in the house because she mentioned that her dads caused her to sleep around in college. Since she was dating Danny when she cremated her mom, this means that it was far after her college life, so she had her mother's dead body ling around the house somewhere, before she finally cremated it.
- Sister - Polly has a lot of family issues with her sister, that are so major, that they become problems with the Judicial Court. She mentioned in the episode Watching The Baby, that she was filing a restraining order against her because she keeps harassing her boyfriend. Her sister was the first and third wife of Polly's boyfriend at the time and that made her believe that she had a claim on him, which Polly disagreed with.
- Danny - Polly's first known boyfriend is a man named Danny, who was shown to be her ex in the episode Hot Tub. He, like Polly, is slightly insane. When they thought they would be in a serious relationship, they mixed the ashes of the family and pets they cremated, which includes Danny's father, Polly's mother, Polly's deceased cat, and a dog they bought together. When Polly broke up with him without saying goodbye, Danny became extremely depressed and when Polly demanded the urn back that held her mother and cat inside, he refused because his father was also in the urn forcing Polly to use Malcolm to steal back the urn, this drove Danny to insanity and threatened to hurt Malcolm if he and Polly didn't surrender the ashes. This scared Polly and Malcolm so much they tried to hide while using Malcolm's car even though he was being punished and wasn't allowed to drive, it was revealed that Danny was in the car the entire time and Malcolm realized that the urn wasn't the problem they were facing but their relationship after seeing them argue. Malcolm threw the ashes out the window and convinced them to solve their relationship. It is unlikely that she got back together with him afterwards because she would soon start dating Abe and Craig in Polly in the Middle. In the episode Watching The Baby, Polly mentioned that she had a boyfriend, who may possibly be the same person as Danny. She said that her sister was his first and third wife and that she kept coming to her house to harass him, which led to her filing a restraining order against her.
- Abe Kenarban and Craig Feldspar - In the episode Polly in the Middle, Polly dated Abe Kenarban and Craig Feldspar at the same time. She loved them both because she stated once that she prefers to date "big" men (fat men). Lois and Hal behooved her that she needed to make a decision between the two, but she couldn't make up her mind. She said that "If society wasn't so hung up, she wouldn't need to make this decision.", implying that she dreams of having a polyamorous relationship, which might have been a joke on her name being "Polly". Eventually, they both found out about each other and got into a fight. When asked to make her final decision, she chose neither of them because they were a distraction from her true career in babysitting.