Gary the Conqueror and his girlfriend, Jennifer, called into the show to discuss their relationship. Jennifer told Howard that she's smart, even though she didn't graduate from high school and, at 5'7", she weighs 160 pounds. Howard then wondered why Jennifer spent time in jail recently, which she said was because she wrote one bad check. When Jennifer claimed that "everyone was doing it at the time," Robin asked her who she knew who was engaging in such behavior. Jennifer responded that she used to hang out with drug addicts, but that she's since cleaned up her life.
Jennifer noted that she's known Gary for 13 years and they've been dating for the past few years. Jennifer admitted that, when she first met Gary, she never envision herself being with him, but that she now loves him. After Jennifer pointed out that one of the qualities about Gary that she likes most is his tendency "to say smart things that blow her away," Artie commented that he found it hard to believe that Gary possesses such an ability.
Jennifer claimed that she and Gary do really have a sexual relationship and that, because of his lack of experience, he didn't last very long at first. However, Jennifer also said that Gary's "gotten better" over time, even though he still hasn't been able to bring her to orgasm. Upon hearing that Jennifer refuses to have oral sex with Gary, Howard had Jennifer give the phone to Gary, and told him to demand that Jennifer use her mouth on him while they were on the air. Because Jennifer refused to do it, Robin commented that she didn't think Gary and Jennifer were actually physical with each other. Artie added that he got the feeling Jennifer was setting Gary up, a statement Robin agreed with. Jennifer then got back on the line and insisted that she's not operating a scam and that she's in love with Gary. To illustrate her point, Jennifer said she'd make out with Gary on the air, but, after allegedly making out with him, Howard pointed out it sounded to him like she was eating an apple.