Herman becomes enmeshed in a web of lies of his own making when Meredith, a former classmate turned woman reporter, shows up to do a "Where are they now?" story on Herman's less-than-stellar life.

While working late to finish a project, Herman eavesdrops on Heddy and her date. After finding out he is married, Heddy turns to Herman for solace. They eventually wind up sleeping together in Bracken's office, but don't know how to handle the affair the next morning.

Herman meets famous Pulitzer-winning writer, Russell Boswell, who Herman admires because of his no-holds-barred pursuit of the corrupt. But when Herman becomes involved in Boswell's own not-so-ethical investigation of a Senator, he has second thoughts.

Herman and Jay go undercover to get a story on a princess, but Herman soon falls in love with her.