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.

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.