When Kenny, Jimmy and Shannon head back to school, Kenny decides to start the first LGBT club at St. Barklay’s in honor of National Coming Out Day. After only recruiting one meek lesbian named Allison, Kenny pressures her into coming out to her family and ultimately realizes everyone’s journey isn’t as easy as his own. Meanwhile, Eileen realizes she might have real feelings towards VP Murray, unfortunately Pat also befriends him, which leads to an awkward situation.

When Halloween arrives, or what Kenny refers to as “the gay Super Bowl,” he plans to go to Boystown to watch the festive costume parade. In an effort to prevent Kenny from attending, Eileen agrees to let him throw his own Halloween party at home. Eileen’s tolerance is ultimately tested when Kenny recruits Stuart and his gay friends to join the big party, and he makes a BIG costume change. Meanwhile, Jimmy and Shannon plan to pull off an epic Halloween prank.

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.

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.

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.