While Brian gets into the cheerleading squad, Lauren feels miserable because she didn't get a part in the school play, which makes her worry about her popularity. Bill and Judy go down to the school to try working things out, and Bill finds out that Lauren's drama teacher went to high school with him. Convinced that she's offering herself to him, Bill decides to let her down. When Lauren's part gets cut from the play, Judy tells Bill to seduce her teacher and get her back on the play. But Bill eventually finds out that his former high school fling is now a gay woman, and Lauren's participation on the play has nothing to do with it.

Judy's fear that Lauren is hanging out with the wrong crowd is confirmed when Lauren gets caught shoplifting. Although Judy doesn't believe Lauren's claim of innocence, Bill convinces her to give their daughter the benefit of the doubt. When it seems that Lauren has stolen again, Bill and Judy's parenting abilities are pushed to the limit.

Bill and Judy feel they need more faith in their lives after meeting the very religious parents of Lauren's boyfriend.

To give Bill and Judy a much-needed break, Judy's parents come to take the kids for the weekend, but decide to stay when they realize Judy is sick. Having forgotten the joy of being taken care of, Judy conveniently extends her illness a little longer but gets into trouble when her parents find out she is faking.

When Bill's mother, Louise, introduces the family to her new boyfriend, Johnny, Bill is ecstatic that she has someone to occupy her time. But the happiness is short-lived as Bill and Judy become suspicious that Johnny, an investment counselor to senior citizens, is bilking Louise out of her life savings. So, the Miller twosome arrange to have dinner with the guy, during which they start to put aside their worries about him – until he squeezes Judy's rear end.

When her cat dies, Linda starts treating her latest loser boyfriend more like a feline than a man. Meanwhile, Bill and Judy can't help but make fun of the strange circumstances of the cat's death.

Bill gets caught up in a fantasy card game in which players pretend to be wizards and warlocks after he learns that Brian is a champion player. Meanwhile, Judy starts spending time with Fitz now that Linda is engaged and doesn't have much time for her.

When the Halversons belittle Bill and Judy's ability to contribute to the school's silent auction, the Millers retaliate by coming up with the hit item. Impressed with the Millers' generosity, the Halversons offer to help Bill and Judy run the event that they donated. But when the Halversons back out on them, Bill and Judy decide that revenge is in order.

Judy is tricked into doing more group activities than she planned when she tries to improve her relationship with her mother-in-law against Bill's advice. Judy is thrilled when Louise invites her on a cruise only to discover, to Bill's delight, that her sneaky mother-in-law has duped her. Now, Judy finds herself traveling with Louise's women's group, The Red Hat Society, which consists of women aged 50 and above. Judy must somehow find a way to let Louise down without hurting her feelings.

Bill and Judy are elated when they discover that Brian actually has a girlfriend, but Bill is even prouder of his son for having a crush on his girlfriend's hot pal. Bill and Judy both have their own thoughts on how Brian should handle his love triangle. Judy wants her son to do the right thing, while Bill, speaking from experience, advises Brian to stay with his plain girlfriend in order to appear sensitive and score the hottie. Meanwhile, Tina retaliates against Linda for scaring her.

Bill convinces Linda to take his advice instead of Judy's when he tells her to let her fiancé pursue his dream of making a music video even though he hasn't written the song yet. At first Judy enjoys the down time she has now that her sister is going to Bill for advice. But Judy finds herself with her hands full when Perry decides to postpone the nuptials and spend all the wedding money on the video. Meanwhile, Brian agrees to let Lauren give him a makeover in order to impress a girl, and ends up missing half an eyebrow.