Bill proves himself too eager to please when his master-of-the-guilt-trip mother pays a surprise visit. That is, until Judy suggests he stop placating the woman and start ignoring her, a strategy that ends up backfiring on Bill when he hurts his mom's feelings and she runs away.

Judy is excited to host Christmas in the Miller house for the first time, but her plans are scrapped when Bill's mom insists on having Christmas dinner for the entire family in her tiny apartment. Meanwhile, Linda's good deed for Christmas – making over her helpless co-worker – goes better than planned when her ""patient"" turns out gorgeous and lands a date with a rich lawyer Linda had her eye on.

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.

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 so ecstatic to hear that Bill's mother, Louise, is going to marry her boyfriend that Judy agrees to be her maid of honor. However, the nuptials are put in jeopardy when Louise's ex-husband, Al, wants to stop the wedding and win Louise back. Meanwhile, Linda is disheartened when Perry continues to postpone their wedding due to his music career.

Judy tries to stand her ground when Bill's mother tries to hone in on her Mother's Day tradition with her own mom. Judy finally convinces Bill to take Louise wherever she wants to go while she, Helen and Lauren go to their traditional tea. But chaos ensues when they all convene at the same place.

After Louise's husband kicks in money towards a Sweet Sixteen party for grand-daughter Lauren, she feels this means she gets to run the show. Meanwhile, Brian struggles to get money for a college application.

With Brian facing a failing grade if he can't climb a wall, Bill's attempt to fix the situation ends up hurting rather than helping. Meanwhile, with Johnny in Japan, Louise decides the family should learn crafty skills, such as needlepoint.

Louise winning a car during a taping of Oprah puts a rift between her and Judy. Meanwhile, Brian and his meteorology club friends decide how to spend a club surplus.

When Judy discovers Al has told his fiance that he's a millionaire, Bill confronts him, but it turns out Bill's the one who's been lied to. Meanwhile, Brian seeks a way to help pay for college.