At first glance, Ray Drecker seems like an ordinary divorced dad who’s facing tough times and trying to make ends meet. But Ray’s got one extraordinary, God-given gift – call it his “winning tool” – that sets him apart from other underpaid high-school teachers. With a little help from an unlikely business ally named Tanya, Ray is about to hatch an inspired plan to ride his winning tool all the way to a more productive, debt-free life.
01 - Just the Tip
Ray, Tanya and Lenore’s new partnership starts inauspiciously when Ray “holds back” during a tryst with a pregnant client.
02 - Tucson is the Gateway to Dick
Ray irritates Lenore by giving Claire marriage advice, Tanya tries to prove she can land a big fish for Ray and Ray pays for the baseball team’s transportation, raising Mike’s suspicions.
03 - Mind Bullets or Bang Bang Bang Bang Motherf***er
Ray and Jessica face separate identity crises and Tanya seethes at her new boss and at Lenore.
04 - Sing It Again, Ray or Home Plate
Ray gives Lenore an ultimatum, Tanya suggests a new hobby to shake Damon out of his doldrums and Jessica faces a quandary at home.
05 - A Man, a Plan' or 'Thankyou Jimmy Carter'
A family emergency forces Ray to recruit a “pinch hitter” for an important client.
06 - Beaverland
Jessica turns to Ray for help with a rodent problem and Charlie helps Tanya come to terms with her guilt.
07 - The Middle East Is Complicated
A new client forces Ray to choose cultural sides and Lenore seethes after learning of Tanya’s duplicity.
08 - "Third Base" or "That Rash"
Ray steps out of the coaching box, Tanya’s deception is exposed and Jessica scratches an old itch.
09 - Fat Off My Love or Im the Allergen
Mike accuses Ray of betrayal, Ronnie vents his frustrations and Tanya lashes out against her co-workers.
10 - Even Steven or Luckiest Kid in Detroit
Ray eyes a possible second chance with Jessica and Tanya tries to make amends for her duplicity.