Best friends Cooper and Olivia are in desperate need of money. A friendly wager over Cooper's matchmaking skills leads to them starting up a dating service.

An Interior Designer is set up on a date with an architect. They visit a house together on their date. They are informed by the housekeeper that the house is haunted.

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.