During season five, it is gradually revealed that he and Samantha have gone on different paths. In episode 5.01, "Veritas", and later in episode 5.07, "Dead Inside", their differences become even more obvious. They care deeply for each other even though he makes it known to her that he disapproves of her "clubbing and drinking" lifestyle. In season 8, it is revealed that she has turned her life around but is unable to find a job due to her prior arrest record. Flack calls in a favor and gets her a job in media relations at the NYPD (episode 8.05, "Air Apparent").