Olivia sets up a date between a nerdy math professor Ryan Lundy and a soap opera star Andrea Johnson. Cooper and Olivia hire an assistance named Gladys.

A Black Tie client, Andy wants to have a date with a model found on page 19 of a fashion magazine. No one knows her name or the agency that she is with. They have to find her first before they can set up a date.

Ryan wins a bet and ends up in bed with Cooper. Olivia gives Ryan a makeover to give him a real chance at Cooper. Black Tie gives a plumber a makeover and sets him up and Andrea Johnson.

Ryan has quit his job, leaving the dating service as a huge unorganized mess. Desperate, they hire Gladys, the man-hungry secretary who previously held the job. She inadvertently sets up the spicy Candy (who had asked for a wild man) with a shy, repressed man, but after a car wreck and some time in jail, they find some common ground. Olivia goes out on her best date yet with Charlie, while Cooper tracks Ryan down at a chicken shack and convinces him that nothing happened between herself and her old boyfriend. Ryan returns to work and Gladys, who had been using their phone line as a phone sex service, quits.