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.

Anne offers to set up Ryan with a new acquaintance, Talia, a recent widow struggling to find her emotional direction. When the three go out together, Talia ends up heavily flirting with them both. Meanwhile Lauren accidentally attracts a man away from Yolanda who has gone on an Asian singles cruise to find a man for herself.