After taking some time to deal with the death of his wife, sportscaster Ryan King is ready to push his feelings down and get back to work. However, Ryan's boss, preferring that Ryan work through his grief first, refuses to let him back on air until he gets counseling. Reluctantly, Ryan joins a support group, where his lack of interest in healing not only makes therapy interesting but also may just serve as the breath of fresh air needed to get his fellow group members back on track to health.
Worried that his career is in shambles, Ryan travels to New York with Steven to interview as host of a national show, set up for him by Anne. Meanwhile, the group grumbles they're getting nothing out of their sessions and blame Lauren to such an extent that Yolanda and Sonia make up a big problem for her to fix. When both plans crash, the group finds renewed strength from their failures.
Ryan finds a new rival in the K-Ball Mascot. Also, Ryan is unsure how to handle a flirty, drunk-dial call from his secretary Carrie. In a strange role reversal, Ryan becomes counselor to Lauren in her confused love life while the group prepares a bachelorette party that will never be.
Ryan dates a recent widow. Serving as his "wingman" is Anne, who ends up competing against Ryan for the widow's attentions. Elsewhere, Lauren unwittingly lures a man away from Yolanda.
Although his radio show is tops in the ratings, Ryan still can't find personal happiness. He pursues inner peace by trying to romantically connect Danny and Sonia, but she has eyes for someone else. Elsewhere, Owen and Anne explore quirky Mr. K's house.
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.
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