Kenny has a difficult first day at school after having come out.

As the school prom approaches, Kenny tries to think of who the best guy would be to ask as his date. With time running out, Kenny and Jimmy try to come up with the perfect “prom-posal” for the classmates they each have set their sights on. Shannon thinks the idea behind prom is a scam and would rather stay at home, but once Pat discovers she was asked to attend, he tries to convince her to go. Meanwhile, Eileen tries to keep VP Murray’s romantic attention at bay but struggles to resist.

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.