On Monday's show Howard introduced everyone to Jessi, who had come all the way from Louisiana to meet Richard Christy. Monday night, Richard and Jessi went out on a date to Scores East, along with an E! camera crew consisting of Doug Goodstein and Isaac Mark. With Jessi on the phone, Howard talked to Richard about their date. Richard said it was Jessi's idea to go to Scores and said it was a lot of fun. Howard wondered why they skipped dinner and went straight to the "entertainment" portion of the evening. According to Doug's notes from the evening, they started making out almost right away. Howard read that at one point, Richard scolded Jessi for drinking her wine before they had a chance to toast when she was only tasting the wine before the wine guy poured for both of them, (as is customary with good wines). Howard played a funny clip of a slightly buzzed Richard and Jessi trying to sing some Poison song together. Howard said that two Scores girls, Jiselle and Taylor, brought them back to the President's club after they ate.
Howard said Richard had gotten Jessi's shirt off and was getting a lap dance from all three girls. Then they switched and Richard gave Jessi a good dance. Howard played a clip of Richard asking Jessi to spank him and then you could hear clothes ripping and Richard said he had gotten his pants ripped down the back. Richard said he had to leave at 12 and Jessi wanted to stay so they arranged with one of the dancers to have her bring Jessi over to Richard's apartment later. Richard said he had dreams of waking up to Jessi and the Scores girl later on that night -- but it never happened. In fact, no one showed up. Jessi said she got side tracked and then it was too late and she didn't want to wake Richard up because he had to get up early for work. Artie told Richard not to let the good looking people out of your site once you've got them with you. Jessi said she had a great time and would love to come back to continue the relationship. Howard wasn't sure she wanted to come back to continue a relationship with Richard or the Scores girl. Artie agreed that there was probably some sex involved during this date, it just didn't include Richard.