Drew is shocked when his obituary appears in the newspaper. He learns that Mimi is responsible; his doctor sent a death certificate to Steve when Drew was in the coma, and Mimi retrieved it from the mail. Her actions trigger a ""doomsday"" prank that Drew had arranged in the event of his early death. She gets handcuffed to a chair and has to watch half-naked fat men dance around. Mimi sends the death certificate out and has Drew's credit cards and bank accounts cancelled. Drew becomes depressed over his brief and unspectacular obituary. Lewis and Oswald reveal that they took out a life insurance policy on Drew in high school, and have received a large claim. Drew points out that they are breaking the law. They promise to return the money after he is declared alive, but will spend the profit they made betting it on the horses. Wick is able to take time off as a ""bereaved spouse"" and go to Hawaii. Drew fears that he has wasted his life, as he seems to be helping more people throu

Milan fixes up Drew with her mother, Lindsay, because she wants her to finally meet someone who isn't just after her money. Drew makes the mistake of allowing Lindsay to drive his car, and they are trapped for several hours after she crashes into a ditch. Lindsay finds Drew's lifestyle charming, and wants to continue seeing him. She is scheduled to leave town a few days later, but suddenly announces that she is moving to Cleveland. Drew is alarmed to learn that Lindsay would lose her $500,000 per month alimony if she ever re-married. He predicts that she will soon grow tired of the novelty of living like a poor person. He challenges her to spend one week in his world. She tries her best to adjust to a simple lifestyle, but really doesn't take to it. She begins breaking out in rashes and losing her hair. Drew decides that he is in love with Lindsay for some reason. After he tells her this, she announces that she is leaving. She never really liked him that much, and cannot sur

Drew's bosses ask him to do a live commercial for the web site during the Super Bowl broadcast. Unfortunately, Drew's nerves get the better of him whenever he has to appear on camera. His attempt to correct this leads to a disgusting mishap that is broadcast worldwide.

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.

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

As a sign of support, Drew pledges to stop drinking for the duration of Kellie's pregnancy, but soon finds it very difficult to keep his promise. Meanwhile, Mimi has the hots for a handsome delivery man; and Oswald becomes part-owner of the Warsaw.

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.

Drew has trouble getting romantic with Kellie after a photo of the baby puts a lot of very strange ideas in his head.

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

Lewis is depressed due to breaking up with his girlfriend so Drew and Oswald take him to a strip club where he suffers a breast related injury. Drew gets caught lying to his girlfriend about the club when Lewis sues the dancer.

Drew comes up with a plan to open a retro store, and seeks a partnership with the now-wealthy Wick. However, all of Wick's funds come through his father-in-law, so Drew must help cover up Wick's extra-marital affair or lose his financial backing.