After Liz takes her ex-boyfriend, Dennis, back simply because he asks, Jack takes it upon himself to mentor her as he thinks that she is leading a life of mediocrity. Meanwhile, Tracy gets a tattoo in the face, Jenna gets botox and collagen injections, and Josh is given two black ...

Charlie gets tired of Alan's mooching and reaches the breaking point during the brothers' double date. Jake is left home alone for the first time.

After being pressured by Jack to plug GE products into her show, Liz integrates Jack himself into a sketch. While Jack hones his questionable acting chops, Frank and Toofer trick Jenna into fearing for her job, and Liz wonders if Tracy is faking illiteracy to skip out on rehearsals.

Alan suffers from insomnia. He visits his psychiatrist, who reveals that the cause of Alan's sleepless nights is his jealousy towards Charlie, and his inability to glide through life.

Berta's daughter, Naomi is pregnant and Berta drags Charlie with her when she confronts the baby’s father. Alan reveals a secret fetish.

Liz struggles to keep Jack out of the writers' room, and Kenneth learns that working for Tracy may be more than he expected.