Paul and J get a call from their manager Rosenberg who tells them that Ashton Kutcher wants to meet with them to discuss possible future projects. When Juicy asks about what kind of money is involved, Rosenberg warns him to not jump immediately to the money portion of the conversation.
Later that afternoon the guys meet up with Ashton at his production company, however the business portion of the meeting doesn't last long. When Ashton's assistant Chrissie accidentally walks into their meeting, she immediately catches Juicy's eye. Ashton tells Juicy that if he can get Chrissie to agree to go on a date with him, then he will hand over his old two-way containing the phone numbers of every major Hollywood starlet. Not to be one to back down from a challenge, Juicy leaves Ashton's office in search for Chrissie. When he finds her, Juicy asks her on a date, she accepts and gives him her phone number.
That night while everyone is fixing their dinner, Computer reminds Juicy and Paul that they are overdue for their annual physical. The next day after a series of tests, their doctor informs them that they need cut back on fatty foods, and spend more time exercising.
When Juicy and Paul return from their physical, they are blown away by the large quantities of fattening food that Computer, Triece, and Pat have arranged for dinner. In an effort to try and get everyone on the health kick, Paul and Juicy announce there will be a competition to see who can loose the most weight within the next seven days. At the end of the following week, whoever has lost the most weight will be awarded five-thousand dollars in cash.
That night while Computer, Triece and Pat are gearing up for their contest, Juicy is busy getting ready for his date with Chrissie. Things, however, don't go as smoothly as he had originally planned once he arrives with Chrissie at a trendy L.A. sushi spot. When Juicy tries to convince Chrissie that he is a very respectful young man, she calls him out and references some very sexually explicit old-school Three-6 Mafia lyrics. Juicy has no rebuttal, and winds up going home by himself.
With the contest in full swing, Pat, Computer and Triece are doing whatever they can to try and loose weight. From visiting a colon cleansing center to hitting the gym, and working out in the back yard, each member of Three-6 Mafia's entourage is eager to win the big cash prize. After a week has passed, Juicy and Paul hold the final weigh in to determine who the winner is. After all three guys have been weighed, it is determined that Computer is has lost the most weight and will be receiving the prize.
The next day, Juicy receives an express package from Ashton, who has made good on his word and sent over his old two-way. After going through some magazines, Juicy decides to call Kristin Cavallari, from Laguna Beach, and ask her on a date. Kristen is skeptical at first, but after double checking with Ashton, she agrees to meet with Juicy for one date. When Kristen meets with Juicy she is initially impressed with his jewelry, but has trouble taking him seriously throughout the course of the date. When Juicy asks her to come back to his place to party with him, Kristen giggles and tells him she is too tired.
By the end of the night Juicy finds himself arriving home by himself for the second time in recent history. Computer tells him to cheer up, and brings him to the back yard where there are two beautiful bikini clad models from the gym waiting in the hot tub. Eager to get his party on, Juicy tells the girls that he wants to show them the hot tub inside the house. Juicy and his new friends make their way into the house, leaving Computer with and empty hot-tub.