With the arrival of their fifth child, Lois and Hal search for a "creative" daycare solution.

Hal, Reese, Malcolm, and Dewey go into business selling Christmas trees, with the boys using some of their own money, but two priests send homeless people to their business, trying to sabotage their sale.

Hal sets up Abe Kenarben on a blind date with Jaime's babysitter Polly but then realizes Lois has also set her up on a blind date - with Craig. Malcolm, Dewey (with his "lucky" shirt) and Reese also meet Reggie Jackson and Francis is embarrassed by Piama in front of his co-workers.

Reese's new girlfriend Beth is about as dumb as he is. Malcolm initially dislikes her but they soon get to like each other too much and Beth breaks up with Reese. Devastated, Reese runs away and joins the army under the false surname.

Hal is named executor of his neighbor's living will and must decide whether to keep him on life support or pull the plug. In attempting to make the decision, Hal discovers he is incapable of making decisions on his own because he always defers to Lois. Meanwhile, Craig asks Malcolm, Reese and Dewey to teach him how to fight dirty since a bully from his childhood is coming to town.

Reese befriends a pack of troublesome stray dogs; Dewey feels conflicted when he starts seeing another mother-figure; Hal unwittingly becomes a motivational speaker.

Malcolm receives a check for $10,000. After Hal and Lois find out, they decide to keep the money and spend it on something for themselves. However, when Dewey overhears this, he wants to get in on it, too. Now, they'll have to find a way to pay Malcolm back.

Hal's friend Trey tells him to come to his dental office when he looses a tooth during a poker game, but their friendship becomes in jeopardy when Hal's faced with a $2,000 bill and causes a fight between them. Reese, meanwhile, teaches Lois how to ride a bike, while Malcolm and Dewey find sleeping as their new favorite pastime.