Drew proposes marriage to Kate and she accepts. Mr Wick makes a mistake so he fires Drew. Drew decides to make it an opportunity to get his ideal job. Kate also gets a new job.
Drew's rich Uncle Cecil, a movie buff, dies, leaving $10,000 to Drew on the condition--based on Buster Keaton's "Seven Chances"--that he get married within 72 hours. Drew and Kate are already engaged, so a quick wedding should be simple, except that Oswald and Lewis get involved, and things go haywire.
Mimi wins a partnership in Buzz Beer at Drew's kitchen table poker game, and she makes changes in the company. Then the crew discovers $2000 missing from the till.
Drew tells Lewis and Oswald of secret shopper jobs so they quit their current jobs. Then Drew learns there is only 1 position so the 2 compete. Many "Whose Line Is It?" cast appear doing improv dialogue and songs and Jay Leno appears.
Drew and Wick get a sham civil union in Vermont so Drew can get his job back and Wick can stay in the US. But the sham marriage threatens Drew's involvement with a Trail Scout troop.
To cheer up Drew, Steve introduces him to Jenny. They hit it off but then Steve reveals Jenny is Mimi's cousin. Kate discovers Drew has moved on and gets drunk with Wick. Drew and Jenny go back to Drew's place, as well as Kate and Wick.
Oswald is not willing to trust his dad, Roscoe, after he is released from prison. Roscoe gets a job selling properties in a resort residential development. Drew works there part-time. But Drew discovers the property company is questionable.
After a car accident, Drew is in a coma. His family and friends try to bring him back from the coma while Drew is in Purgatory with beautiful women where he wants to remain.
In an effort to show his nephew that Mimi will be a good mother, Drew (who is still in a coma and on his way to heaven) takes his nephew's place as Mimi and Steve's newborn baby for a few hours.
The local paper runs an article indicating Drew died in the accident that put him in a coma. In spite, Mimi sends his death certificate to his credit card company who freezes his account. Searching meaning, he volunteers at a crisis center.
Drew gets a hot chick because of his new motorcycle and a leather jacket. And while he loves her attention, he finds he has to constantly work to keep her from seeing that his image as a bad, tough guy is not real.
Kate introduces Eric to the gang and Drew is jealous, causing friction with snarky comments. For Steve, Mimi and Drew call a truce but find it very difficult to abide by.
Drew shows Lewis how horrible he has been to other people so he will change. Lewis is convinced of his evil ways and determines to change the others so they will also get into heaven. In usual Lewis fashion, he takes this to the extreme.
Oswald contracts to deliver Easter baskets for Winfred-Lauder with a partner but then gets greedy and decides to go it alone. When the chocolate Easter bunnies melt while being stored in Drew's basement, the foursome rally to make delivery.
Drew meets a cute chick who is also interested in him but he discovers she is an activist who protests Lewis' employer DrugCo. Lewis feels betrayed and tells Drew she is just using him to get info about a secret DrugCo project he is on.
Drew starts seeing a cute chick who is compulsively politically correct (health food, hemp clothing, recycling, etc). The Buzz Beer partners plan a barbecue to boost sales but Drew tries to hide the fact from her they plan to grill burgers.
Winfred-Lauder approves Drew's idea of a women's store and puts him in charge of setting it up and running it. With so much to do to get the store open, Drew starts seeing bizarre things. Lewis and Oswald get jobs at a fireworks company.
Drew has been committed to a mental ward. Lewis and Oswald find him there but are not allowed to see him because they are not family. So they have themselves committed but now they are stuck in it themselves. Lewis plots a stupid escape.
