Portrait of a Lady

S1 E1: On her first day at Gruber and Gruber Helen consults with Ruth O'Malley (Alison Whyte) who wants Helen to enforce the 'vasectomy clause' in her mother's will. The clause states that Ruth's brother Dean, a free-spirited artist, will only inherit his share if he has a vasectomy. Roz calls Helen's old boss and finds out that Helen was fired from her last job but she agrees to keep her on if Helen will submit to some mentoring. Helen gets an after-hours visit from Dean O'Malley (Glenn Robbins).