S1, E18: Ryan, still pained from the breakup with Simone, backslides into his old gambling habit, though sternly warned by Lauren to steer clear. But when he receives the life insurance check for his deceased wife, it's more than he can bear and he starts making bets on anything and everything. Meanwhile Anne meets a stunning, young bookstore clerk, Brittney, who turns out to be all beauty and no brains. Lauren comes to Ryan's rescue by fleecing him at poker and in the aftermath, Ryan bonds with Anne over their respective lost loves.