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- Mild-mannered bookstore owner George's life changes when his daughter-in-law's estranged father, Leo, a magician on the run from mobsters after stealing casino money, seeks refuge in George's spare room.
- Four best friends troll for girlfriends for themselves while walking their dogs every day.
- Five slobby friends share an apartment in Manhattan inherited by bartender Randy. Innocent intern Joe is from Iowa, PJ sponges off his parents. DA Johnny and adman Cal are the other roomies. Randy has a crush on building super Tess.
- The penthouse residing Conklin family of socialites and the basement dwelling McBride family of maintenance men find themselves unhappily linked when the heiress daughter and blue collar son fall in love.
- Will Hennessy is an aspiring artist at an ad agency who heads up a group that includes his ex-girlfriend copywriter Liz.
- George and Leo take a parenting class together.
- Alice gets a new, hot roommate. George teaches a business class that includes his housekeeper. The Dean misconstrues that relationship. Leo helps Ted get over the fear of flying.
- On advice from Leo, George attempts bribing a building inspector.
- George wins a free therapy session while Leo starts a fake tour/taxi service.
- Ted and Casey host the baby shower. Robert Goulet comes for a book signing. Leo complicates things.
- Halloween night finds Leo afraid that there's a ghost haunting the bookstore, and George terrified of running out of candy.
- George hires a new, younger housekeeper with boyfriend issues and an angry father. Leo opts to help Ted with buying fish for the restaurant.
- Leo steals from George to give their grandbaby-to-be a savings bond.
- George gets a massage from Tasha, who Leo dates. Leo and Tasha have a bad night. Casey helps Alice get a date.
- Leo and Tasha announce their engagement. A familiar oops occurs during the wedding ceremony. Alice meets a friendly mobster.
- Casey and Ted's child is born. George hires a nanny, Alice. Alice falls for Ted. Leo has trouble bonding with the baby.
- When Leo has a heart attack and ends up in the hospital, his former wives arrive and all stay at George's house.
- A chain bookstore moves into the area and tries to run George out of business. Ambrose starts a new job.
- Leo discovers that George's stamp club is really his weekly poker night. A jealous Leo crashes said game. Ambrose hypnotizes Ted. Earl's marriage is on the rocks.
- Ted swings for the fences when he hears a restaurant critic will be reviewing the restaurant.
- George helps Leo to stop smoking cigarettes. Ted learns of Casey's smoking hot ex.
- Casey asks George for investing help. This prompts Leo to go to business school. Leo's teacher dates George.
- George hosts the Stoody's Thanksgiving. Leo dates George's niece. Ted and his brother air their grievances.
- Casey decides to call off the wedding as a result of cold feet.
- George decides to date again. Everyone has advice. Leo thinks George's date has ties to the mob.