According to Us, Jenner’s friendship with Pratt become rocky after Pratt was quoted by Details magazine making insensitive comments about Jenner’s ex-girlfriend Nicole Richie. Pratt told the magazine that he had convinced Jenner to date Richie so that he could "get that skinny bitch to eat, all right? You are about to become The Guy Who Got Nicole Richie to Eat. Process that sh--, bro. You'll be, like, a f---ing hero to America." Obviously, the article resulted in a mountain of bad press for both Pratt and Jenner.

But the friendship ultimately ended because of Jenner’s insistence on remaining in Conrad’s life. Because of the bad blood between Pratt and Conrad, Pratt told Jenner to choose between the two of them. Jenner chose Conrad. Pratt told Us, “I wish them both the best. [Conrad and Jenner] are meant for each other.�?