Liz is caught off guard when Jamie stops by her office to ask her out on a date. He guesses that Liz is 29. She decides that age shouldn't have anything to do with them not going out because he's 25. Liz goes along with Jamie's assumption that she's 29 and accepts the invitation.
Tracy is coaching a little league team and Jack wants to pitch in and help out. Tracy warns Jack that they practice in the mean streets of Knuckle Beach. Jack purchases new uniforms and makes over the baseball field for the team.
Liz is up way past her bedtime while on her date with Jamie. She finally has to confess that she's 37 and doesn't party in Brooklyn. Jamie makes a confession of his own that he's only 20. Things get worst for Liz when she spots Jack at the same party.
Jack fires Tracy and makes Kenneth the coach of the little league team. Kenneth can't control his players when they begin fighting and turning on each other. The players then turn their anger out on Jack and Kenneth and come after them with the new baseball bats that Jack had bought for them.
Jack pleads with Tracy to come back to the little league team. Tracy is skeptical, since Jack was the one who fired him. But, Kenneth admits that Jack screwed up and they need Tracy back. Tracy reluctantly agrees to coach the team again and they begin winning.
Frank has admitted his feelings for Jamie and begins to question his sexuality. He confronts Jamie in the halls about his recent discovery. Jamie assures Frank that he's completely straight and not interested in Frank. Frank later realizes at a gay club that he is definitely straight - just gay for Jamie.
Liz picks up Jamie for their date. Before they leave, Liz discovers Jamie still lives with his parents. On top of that, Liz realizes that his mother looks strikingly similar to her. She ends the relationship right then and there. Jack points out later that at least she had her fun.