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.

While taking a pregnancy quiz with Kellie, Drew recalls his father's death in a fall from the roof. Drew was horrified to discover that he was never even mentioned in his dad's diary, and tried to prove himself by arranging for a lavish military-style funeral. However, disaster struck when George accidentally wound up with a casket featuring the logo for the band Kiss.

After Tony the bus driver gets into an accident, he pleads with Drew to keep it a secret because he is close to retirement and doesn't want to risk being fired and losing his benefits package. Drew cannot do this because he fears for the passengers' safety, so he tries to convince Scott to give Tony another job.

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