The search begins for a Joe DiMaggio to play opposite Marilyn - but everyone's first choice, Michael, has a secret. Karen returns to Iowa for a baby shower and must decide what she wants for her future. Eileen begins rounding up investors - but ex-husband Jerry may already have poisoned the well.

Karen must learn to advance in the high-stakes world of Broadway, as Derek hosts a party for hot young star Lyle. Eileen tries a sly new strategy for raising funds, while Tom goes on a first date.

The team deals with the workshop's after-effects; Derek asks Karen to help him steal the show from Tom and Julia; Eileen's daughter's surprise visit forces her to deal with her ex-husband.

Derek and Karen reach a turning point, so one of them makes a tough decision. Meanwhile, problems emerge in Jerry and Eileen's partnership; complications arise at the "Hit List" debut at the Fringe Festival; and Ivy attempts to save her and Terry's show.