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.
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.
Mike's Christmas spirit gets dampened when Ryan, the father of Kristen's baby, unexpectedly comes back to town after a long absence. Meanwhile, Ed hires Mandy as an elf at Outdoor Man, where she tries to unionize the other elves to get better perks.
Mike, amazed that Mandy might finally have found a passion for something, takes her under his wing at work when she offers to start an Internet campaign to keep Ed's favorite barber shop hangout from closing. Also, an exhausted Vanessa insists that she can still take care of the household despite her hectic work schedule, until she falls asleep during her own business presentation.
Mike is taken aback when he finds out that Ed, who has been an absentee dad, has hired his daughter, Gabriella, to replace him as the new marketing consultant of Outdoor Man. When Ed agrees with Mike that her youth-oriented proposals to re-brand the retail stores aren't the way to go, she plays the Daddy card for all its worth. Also, Mike and Eve bring home a stray dog that Mandy thinks she's allergic to.
When Mike gets NASCAR driver Tony Stewart and his racecar in the store, he realizes how much he misses the adrenaline rush he used to get from his adventures on the road; Vanessa thinks about how she used to take more chances before she was a mom.
When Mike realizes he unintentionally upstaged Vanessa's announcement about being nominated as the top volunteer school parent, his efforts to make it up to her might cause more harm than good. Meanwhile, Eve is afraid she won't fit in at high school; and Ed wants to release an Outdoor Man action figure inspired by Mike.
When Vanessa's sweet but flighty sister, April, comes to visit, Mike knows she's only coming to ask for yet another loan. Mike would rather use any extra money they have to buy a tank so that he and Ed can take it to a junkyard to run over old cars and boats. Meanwhile, when Kristen and Kyle decide to break up, Kyle is more concerned with what Mike will think.