LARRY (John F. O'Donohue). Larry is also in his 60’s and is Rosie’s internet date in the pilot. As a member of 'Love Online', he turns out to be quite the player for his age; like an older version of Carl. After his date with Rosie in the pilot, Larry learns it all catches up with him and New York City can actually be a small city after all.
KELLY (Kelly Sullivan). Attractive woman in her 30’s who works as a profile editor at ‘Love Online’. Kelly lives above Pete and Carl and shares an apartment with her mother, Rosie, who lives half of the year in Florida. Despite working at the country’s number one internet dating service, Kelly’s neurotic behavior gives her a love-hate relationship with men.
ROSIE (Heather Rasche). Kelly’s hip, single mother who is in her 60’s. She joined ‘Love Online’ after Kelly got a job there. Since then, men, internet dating and New York City are the loves of her life as she knows all three will soon be gone.
JOE (Joseph Somma). Good-looking bartender in his 30’s who can’t hold down a steady job. Joe is also a member of ‘Love Online’ and is a compulsive gambler. Joe has lost several dollars and several women because of his gambling habit. Joe still lives with his rich parents in a high-rise close to Pete and Carl.
CARL (Kevin Stapleton). Born and raised in Queens, Carl is in his 30’s and is still quite ‘the player’. His outgoing personality and confidence makes him a hit with the ladies. Carl shares an apartment with Pete and is a longtime veteran of ‘Love Online’. Truly a professional dater, Carl is also a hopeless romantic. He starts the series working for a national cable network.
PETE (Peter D.Michael). Actor and personal trainer with a great personality and a perfect goatee. Pete's funny, very neat and baffled why women seem so complicated. He's definitely a hopeless romantic and has tried to avoid 'the online crutch' for a long time. But, Pete is convinced to finally join ‘Love Online’ after being pressured by his roommate, Carl and their other friends.