Tonight on VICELAND's The Therapist, Chicago rapper Chief Keef sits down with Dr. Siri Sat Nam Singh for a session. The rapper, who recently got out of jail for the second time this year, is encouraged during his session to reflect on his past choices. Singh helps Sosa draw connections between his childhood life and his current situation, to see if the young artist can draw any clues about what has led him to getting into trouble as a young man.

Keef, who is generally quiet and reserved, shared a surprising amount of detail about his home life, remembering a whole slew of cousins that he admired growing up. He shares that many of his family members were recording artists themselves, including Blood Money, who was killed a few years ago in Chicago. Keef is open to Singh's guidance, with the episode focusing on the doctor trying to coax the rapper into shedding his "bad boy" image, and make positive changes in his life. Clearly affected by the conversation, the rapper mumbles, "I didn't see this day coming." It's Keef in a surprisingly vulnerable moment.