When Kenny, Jimmy and Shannon head back to school, Kenny decides to start the first LGBT club.

Kenny starts using a gay dating app; Jimmy goes to extremes to declare his love for Lacey; Aunt Jodi mistakenly believes Shannon needs her help with her love life.

Eileen's tolerance is tested when she allows Kenny to throw his own Halloween party to stop him from going to Boystown to watch the costume parade.

When VP Murray starts spending time around the house, Pat realizes it's time to move out. Meanwhile, Eileen starts her new job at Aunt Jodi's salon, and when the kids discover how unhappy their parents were during their 18 years of marriage, they stage a celebratory "divorce ceremony".

Pat and Eileen invite Gloria and VP Murray as their dates to the O'Neals' Thanksgiving dinner, changing their tradition.

Pat's brother Dwayne (who is also Aunt Jodi's ex-husband) comes to town to help Pat build his new "tiny house" in the garage. Shannon realizes Jodi and Dwayne still have chemistry, and tries to get them back together. Meanwhile, when Eileen becomes addicted to a CrossFit class she's taking with Kenny, he must find a way to break the cult-like hold it has over her.

When Jimmy recruits a reluctant Kenny to join his wrestling team for a one-time match, a surprise victory gives him the confidence to join the team full time to become the first, openly gay athlete at St. Barklays. Kenny's newfound stardom makes Jimmy feel a bit replaced, but when an opponent refuses to wrestle his brother, Jimmy puts his feelings aside and rallies the team around Kenny. Meanwhile, Pat injures his back trying to help Eileen prepare for a weekend getaway, but things only get worse when she tries to be the perfect caregiver to impress VP Murray but fails miserably.

Eileen will stop at nothing to win the Christmas choir competition and gives the coveted Christmas choir solo to their newest member, Brett (Sean Grandillo), to Kenny's dismay, while Jimmy is tasked with spying on their toughest competitor, Sheila Demars (Angela Kinsey). 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, but ultimately discover that the three of them make a pretty good "throuple".

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.

Shannon asks Vice Principal Murray to stand for her at her Catholic confirmation which mom Eillen perceives as just too weird since they are only dating.

Kenny and Brett have officially broken up so Kenny is wallowing in his sorrows by his lonesome at home with no one to share Valentines Day with.

When Kenny convinces VP Murray to hire a gay teacher, Kenny's loyalties are tested when the teacher starts to make Jimmy's life miserable. Meanwhile, when Pat's courteous nature robs him of a winning lottery ticket, he decides to stop being such a nice guy with Shannon's help, which doesn't bode well for Eileen, who needs Pat's help hosting a dinner for the Bishop.

VP Murray talks to Pat about his plans to propose to Eileen; Eileen and Kenny help Allison deal with her close-minded parents; Shannon and Jimmy find a pregnancy test.