Jenna told Liz that she had lied to Jack about her age. Liz burst out laughing when Jenna told her Jack thought she was 29.
Jack gave Liz a lecture on living large. He said that she had to start acting like a winner because he only surrounded himself with winners. To start her off, he gave her a number to a very expensive restaurant in New York. Liz decided to bring Dennis there as a date.
Liz was embarrassed when Jack saw her and Dennis on their date. Dennis kept making immature comments, further embarrassing Liz. The next day, Liz did her best to avoid Jack, but it didn't work. She defended her relationship to Jack, but he really didn't care.
Liz walked into Jenna's dressing room and was frightened with what she saw. Jenna tried to look younger by trying Botox, a chemical peel, and collagen. She thought it made her look ten years younger. Liz just thought she looked scary.
Tracy was tired of magazines calling him normal, so he did something far from it...he got a face tattoo! Between Jenna looking like a porn star burn victim and now Tracy's face tattoo; Liz had no idea what she was going to do with her show.
Josh had admitted his crush on Elizabeth Taylor and was surprised when he heard she had a present for him. Josh was shocked to see Elizabeth Taylor visit on the set. She was mad about his impersonation of her and beat him up for it! She beat him so badly, that Josh couldn't work on the show.
Liz was tired of telling Jack that she didn't need him for a mentor. Liz was tired of people making judgment on the decisions she made with her life. She later admitted to Jack that he was the most stable man she knew. She knew that to begin improvements with her life, she had to dump Dennis.
Liz discovered that Tracy really didn't get a face tattoo and that he had really had it drawn on his face with a pen. She couldn't believe the extremes he had gone through, just to prove he was not a normal celebrity.
Liz's train wreck of a show was saved when there was a huge black out and it had to be cancelled. She went home to break up with Dennis. She found him emotional over the hockey game he was watching and she ended up inviting him to live with her.