Eileen will stop at nothing to win the Christmas choir competition and gives the coveted Christmas choir solo to their newest member, Brett, to Kenny’s dismay, while Jimmy is tasked with spying on their toughest competitor, Sheila Demars. But, when Kenny attempts to sabotage Brett’s role, he finds a potential love interest. Meanwhile, Shannon accidentally gives Pat the wrong impression about a Christmas present she plans on giving to Ethan.

Eileen and Pat’s divorce papers come through, and Eileen realizes she is free to be with VP Murray, but their attempts are plagued with obstacles that make Eileen doubt her desires. Kenny tries to impress Brett by being a “bad boy” and gets a tattoo. Shannon puts out a petition to stop the dissection of frogs at school while Pat realizes that he needs to figure out how to be single again.

After Kenny and Brett officially become a couple, Kenny starts to think of plan on how he should break the news to his parents. Meanwhile, Jimmy surprises everyone when he scores a high SAT score, forcing Eileen to hold up her end of a deal that she had previously made and takes Jimmy car shopping.

Kenny’s jealousy over Brett’s relationship with his best girl friend leads Kenny to realize he’s been a bad friend to Allison. Jimmy and Shannon start their own ridesharing company. Meanwhile, Eileen and Pat are shocked to catch Clive “cheating” on them.

Jimmy wants to teach his younger brother the rite of passage of drinking. When Shannon gets a comp hotel room due to a scam she’s pulling, Jimmy thinks this is the perfect time to teach Kenny how to drink, but it all goes awry when Kenny invites Brett to join in. Meanwhile, Eileen discovers that Pat has a new girlfriend, her nemesis, Sheila DeMars.

When Shannon asks VP Murray to be her godfather leading up to her confirmation, Eileen fears her own relationship with him might be moving too fast. Shannon’s big day also has a surprising effect on Kenny’s relationship when Brett says, “I love you,” sending Kenny into a tailspin. Meanwhile, the return of a hot former babysitter puts Pat and Jimmy at odds when she constantly makes passes at Pat.