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Guest stars throughout season one include: Cybill Shepherd, Jason Priestley, Terry Bradshaw, Nick Carter, Shelley Long, Patrick Warburton, Thad Luckinbill, Billy Aaron Brown and Larry Miller.Cate decides to go back to work as a nurse and Paul has to contend with his oldest daughter, Bridget dating his co-worker Tommy's son Kyle.After seeing how much money Bridget spends on keeping up with the latest fashions, Paul and Cate decide it's time for her to get a job to learn the value of a dollar.
Meanwhile, Paul tries in vain to wean Rory off video games and introduce him to the world of books.It's time for summer vacation, but the Hennessys can't decide where to go.Paul wants to go to their regular cabin at the lake, Rory's idea is Space Camp, Bridget wants to go to Mall of America, Cate wishes to visit her parents' condo while Kerry just wants to stay home. Each family member must give up a bad habit, and the last person standing gets to pick the vacation.Paul seems to be the only one looking forward to a family Halloween, as Bridget, Kerry and Rory make plans to spend the spooky evening away from home and with their friends.
But Paul's wish to relive the past by having the family get together for one last Halloween campout in the old treehouse may turn out to be the biggest nightmare of the evening.
Meanwhile, Kerry's first date turns out to be a dream, but she is devastated when the boy doesn't call her back.