Liz was uptight and taking her rage out on the staff of TGS. Jack called her into his office and offered a solution. He wanted to give her a little companionship by setting her up with a friend of his who was from out of town. Meanwhile, Jack also invited himself to Liz's poker night.
Liz agreed to go on the blind date. Jack gave her money to buy something nice to wear. While she was heading out of the office, the guys all gathered to play poker. Jack was ruthless and won every hand. That included taking a wedding ring and Emmy that were placed as bets from the players.
Much to Liz's surprise, Jack had set her up on a lesbian blind date. Gretchen said that she had no interest in turning a straight girl gay. Liz said she would stick around for dinner though. The next morning Liz asked Jack what made him think she was a lesbian; he told her that it was her "bi-curious" shoes that gave it away.
Liz was flattered when she heard that Gretchen really liked her. The staff thought it was hilarious that Jack thought she was a lesbian. Later that night, Liz decided to give Gretchen a call and they set up a dinner date.
Determined to beat him at cards, Jack scheduled a re-match with Kenneth the page. People watched as Jack challenged Kenneth to wager his NBC jacket and job. Jack won the hand and got to take Kenneth's jacket and job from him. Jack admitted he wasn't really going to fire Kenneth, but wanted to prove he could beat him at cards.
After another night out, Liz and Gretchen started calling each other Oprah and Gayle because of their friendship. Gretchen thought it was time to take a break from Liz. She said she felt she was being led on by Liz and reiterated that she did not want to chase a straight girl.