Jacks attends a dinner party with his girlfriend and asks the millenials to act as his inner circle of friends so his girlfriend doesn’t get concerned.
Jack dates a millennial, but has trouble keeping up with her exhausting lifestyle and enlists Clark, Emma and Mason to help him adjust.
Jack insults Brook’s fiancé at a re-engagement party and botches his attempts to apologize. Also: the millennials get into a squabble over who should create a slideshow for the party.
Mason becomes famous for an investigative coup, but Jack grows jealous and tries to reassert his dominance. Also: Clark has trouble asking out Emma, so he gives her relationship advice about other guys instead.
When Mather, the president of the Chicago Adventure Society, accuses Roland of faking the story of the expedition that made his career, Jack, Brooke and the millennials team up to clear his name. Also, Clark is dumbfounded when he notices that Jack seeks Mather’s approval the same way he seeks Jack’s,