George's daughter brings Ruth some relief; Brenda gets a rude awakening on the first day of her internship; a freewheeling artist is puzzled by Billy's cautious career path; David asks Claire for a difficult favor; and Nate finds he has little in common with an old friend from high school. Maggie: Tina Holmes. Sharon: Jenna Fischer. Tom: Sean O'Bryan. Wolf: Rhys Coiro.