Howard began the Hottest Regular Chick contest by welcoming fellow judges, Ralph and King of all Blacks, noting that, since JD and Fred couldn't get a girl to participate, they were already out of the competition. Artie said he found his chick, Diane, right in front of the building with her husband. Despite the fact that she's 43, Artie offered her the whole $5000. Artie said to take it easy on her because "she's had a couple of babies".
Diane came in and said she recently had twins. Diane said that she's a college professor and psychologist, and added that she thinks Artie needs to make some lifestyle changes.
Ronnie's girl, Amy, came in and said that she wasn't creeped out by Ronnie when he approached her in Columbus Circle. Amy claimed Ronnie was "really smooth and nice", and put her at ease. Amy said she is a sales executive, and has never modeled. Both King and Ralph approved of Amy's ass, even though she claimed she needed "some more work in the gym". Ronnie said he specifically told her she wouldn't have to get naked.
Gary's girl, Jessalyn, came in and got a "holy shit" out of Artie. Howard asked Jessalyn what Gary said the prize was, and she replied "a cash prize". Gary said she's been so sweet to deal with, he now wants to split the $5000 with her. Jessalyn said she was 22 and had just moved here from Ohio. Gary noted that she'd never done any modeling, but did work down at the Hawaiian Tropic Zone restaurant, where work attire is a bikini.
Benjy said he found his girl, Jamie, as she was going in to apply for a job at the Hawaiian Tropic Zone. Jamie revealed that she's Tommy Hilfiger's niece, and that, while Tommy takes her on "nice vacations and stuff", he doesn't give her money. King became upset when he learned that Jamie drove a Mercedes, claiming she didn't need money. Will came in to say that Jamie told him that she'd date Benjy if she were single. Jamie confirmed that she would, but was committed to her boyfriend.
Jessalyn claimed she was a "chick-y hip-hop" dancer, which Ralph wanted to see, so Fred played some Beyonce for her. Jessalyn danced and thoroughly impressed Howard, King, and Artie. For the third time in a month, Artie announced the show had found "the hottest chick we've ever had up here". Ralph requested that Jamie dance as well, and she did, which everyone seemed to enjoy, though Ralph kept requesting more "hip movement".
Robin voted for Jessalyn. Ralph voted for Jessalyn. King of all Blacks voted for Jamie. Fred picked Jessalyn. Howard voted for Jessalyn.