Throughout the SeriesEdit
In The Wednesday Incident, Jake, Gina and Kevin go to the Two Daughters to see if Holt was in a bad mood when he got there. It is revealed by Diane that he was in a very good mood and she is also surprised at how old Peralta is, considering how he acts. Jake says that he's sure Holt vents about everybody on the squad but Diane reveals that it is just Jake that he vents about. Jake is annoyed at this and asks her what she is doing afterwards.
Raymond goes to the Two Daughters for his breakfast everyday and the two seem to be on good terms. Diane mentions that Holt always vents to her about Jake whilst he eats there.