Mike plays Cupid for Mandy by setting her up on a blind-date with Kyle, one of his employees who he thinks would be the perfect guy for her. But Mike's set-up gets off track when Kyle accidentally meets Kristin. Meanwhile at work, Mike's long-time boss and friend, Ed, announces that he's grounding Mike from their catalogue's international photo shoots and putting him in charge of the company's webpage. In this new role, Mike discovers that the Internet might actually provide him just the outlet he needs, a platform that gives him a voice to appeal to those who agree that manliness is under assault, and a pulpit for his opinions about feeling like the last real man in a woman's world.

Mike is outnumbered by his wife and daughters when they all agree that baby proofing the house is a good idea. But soon Vanessa has second thoughts when she finds herself home by herself babysitting Boyd and can't release the toilet seat's complicated childproof latch. Meanwhile, Mike thinks it's time for Mandy to earn her own money and gets her a job delivering pizzas -- without first consulting Vanessa.

When Vanessa forces a reluctant Mike to attend Grandparents Day at their grandson Boyd's preschool, Mike manages to insult the daycare teacher and Boyd gets kicked out of school. Boyd's mom, Kristin, tells Mike that he now has to look after him, so Mike takes the two-year-old to work with him. Meanwhile, after an elderly looking grandmother at the Grandparents Day event thinks she and Vanessa are the same age, Vanessa goes out of her way to look more youthful -- hoping no one sees her buying clothes from a boutique her 17-year-old daughter, Mandy, shops at.

Mike feels let down when his daughters aren't into celebrating Halloween with him the way they used to. He decides that his two-year-old grandson, Boyd, can be his perfect trick or treat partner. But Kristin, Boyd's mother, adamantly tells him that she doesn't want her son to go out on Halloween. Mike sneaks him out -- with a plan to get the child home before Kristin gets back from work. When Mike, dressed as John Wayne from "The Green Berets," gets to Ed's house with Boyd, they are greeted at the door by Ed's lady friend, Elvira (guest star Cassandra Peterson).

Mike must decide which way he will vote when the all-male Outdoor Man's softball team gets a mandate to allow females to play. Also, while helping a reluctant Mandy fill out college applications, Kristin makes some decisions about her own future. Mike hopes Mandy will go to his alma mater of Michigan State, but Vanessa wants her to attend her alma mater, the rival Ohio State.

When Mandy wants to enter a contest to be on a TV modeling show, Mike intends to give her his usual "yes" -- as he does with all of his daughters' requests -- knowing that Vanessa will tell her "no." But when Vanessa insists that Mike play the bad cop this time around, he has difficulty following through.