Tim Gunn stops by unexpectedly, so the staff must juggle guests. Meanwhile, Todd asks Debra Messing to film a video while channeling her old sitcom character; and Randy and Marcus pitch their invention to Mark Cuban.

Staci tries to convince transgender celebrity GiGi Gorgeous to go on a date with Jimmy; Ana pitches her makeup line and wants Stephanie March to be her new spokesperson; Janeane Garofalo is dismayed by Jimmy's sexist sketch.