Recurring dreams of Kate force a heartbroken Drew to forego sleep, until Mimi offers him a surefire way to get over being dumped. Meanwhile, Lewis finds some unsettling common ground with Nicki after taking her out on a pity date.

Drew enlists a professional matchmaking service--operated by his former co-worker, Larry--in his search for a wife. The woman who comes out as his ideal match, Robin, seems terrific; but Drew just can't see himself marrying her. He later winds up falling for a woman on the bus.

Drew finds romance with Dawn, but their new relationship appears doomed because of her past. They can't find any time alone because one of her ex-boyfriends seems to turn up every few minutes.

Drew gives Lewis his Christmas bonus, a used Rolls Royce. However, the flashy car causes Lewis to undergo a strange personality transformation, and he can no longer be bothered to hang out with his longtime friends.

Oswald and Lewis seek revenge against Drew after they discover that he gave away their Christmas gifts--handmade mugs--to a thrift store. Drew winds up getting an unscheduled colonoscopy from a Russian veterinarian.

As Drew prepares to marry Lily, his mother notes how upset Kellie seems and realizes that she has strong feelings for Drew. She believes that Drew feels the same way about Kellie. Drew and Lily go through with the wedding, but the union proves to be a brief one when they realize that they really are not right for each other. Drew winds up sharing a dance with Kellie.

Drew and Kellie's new relationship is threatened by their strong political differences.

Kellie is furious with Drew after he blows off an appointment to see their baby's first sonogram to go drinking with the guys.

Kellie finally agrees to marry Drew, but their wedding plans are thrown into disarray when she goes into labor.