Fiona takes on skittish, suspicious, lottery-winner Steve Olson as a new client in hopes of solving her cash-flow issues. Jerome's promiscuous baby-mama, Gina, calls to complain about her boredom - while he's off using and abusing Fiona's NYC penthouse to benefit baby Angus's education. And Fiona begins seeing a patient whose elderly girlfriend wants him to quit his unusual job.

Jeb Masters calls Fiona to complain about her behavior, since it's bordering on sexual harassment. Philadelphia neighbor, Grace Tiverton, is eager to strike up a friendship and will do absolutely anything to hang out with Dr. Wallice. Gina returns with examples of her new business venture, thanks to Fiona, and Steve Olson finally reveals that it's Fiona who should have trust issues.