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.

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.

The team sets up a date between a corporate lawyer whose looking for something different and a champion surfer. Impressed with they way he handled Cooper, Olivia asks Ryan Lundy to join the team.

Ryan's fantasies life starts to bloom. His first fantasy is Cooper. The teams put together a date that helps the client Helen realize that she unknowingly has affections for women as well as men.

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.

Darcy is a lawyer from Reno seeking a boyfriend, and she is matched to Las Vegas casino employee Nick. Cooper and accompany Darcy to Vegas to meet Nick, where complications briefly ensue due to the appearance of Nick's ex-girl friend, a stripper named Diamond.

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.

The agency helps an aging model concerned about her looks meet a blind man who admires her soul as well as her body. Cooper and Ryan continue to explore their new sexual bliss. Olivia, finally moving on from the death of her husband, finds pleasure with a tall, dark and handsome yoga classmate named David.

Adult film star legend, Ron Jeremy enlists the help of Black Tie to find a woman who doesn't know about his history. It seems the porn star no longer likes it when women only want to sleep with him because he has a large penis. He wants a woman with brains too. He wants to connect too.

Blake Tie sets up a couple of actors on a special date as extras on a soap opera. Ryan puts Cooper to the jealousy test.

The dating service set a saucy romance novelist up with a critic who has ripped her work to shreds, and arranges for the two of them to ride along with some in-on-the-scheme cops. Sparks fly when the two discover each other's identities and feel a mutual attraction. Meanwhile, Cooper picks up a pair of earrings from an old flame, Justin. Although she avoids temptation, a heartbroken Ryan sees them in a final kiss and assumes she cheated on him.

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.