"Adventures in Boss Sitting" is the fifth episode of the fourth season of Disney Channel's That's So Raven and the eighty-third episode overall. It aired on March 24, 2006. It was written by Jessica Lopez and directed by Eric Dean Seaton.
Donna Cabonna makes Raven her temporary assistant while Tiffany is out of town. Devon returns to San Francisco for one night and Raven is planning on a romantic date, but Donna Cabonna shows up at Raven's doorstep in tears because her boyfriend Teddy broke up with her. Raven must juggle both Devon and Donna, running up and down the stairs, catering to Donna's every whim while trying to have a nice night with Devon. Donna breaks down again, and Cocoa runs down the stairs with the head of a bear that Devon got Raven. Devon finds out that Raven has been hiding Donna upstairs, and gets angry and breaks up with Raven. Meanwhile, Cory goes on a date with a girl named Brittany. At the movie he sees Cindy, his ex-girlfriend, who is also on a date with a boy. The date doesn't turn out all that well, and Cory finds himself wanting to get back together with Cindy. Cindy, Devon, and Teddy, all come to the door and each relationship is rekindled.
- Raven-Symoné as Raven Baxter
- Orlando Brown as Eddie Thomas
- Kyle Massey as Cory Baxter
- Anneliese van der Pol as Chelsea Daniels
- Rondell Sheridan as Victor Baxter (absent)
- The title of this episode shares a similar name with the Raven's Home episode "Adventures in Mommy-Sitting".