Kate wants to go skiing, and Mike doesn't have the money. He finds a bargain - if twenty rooms are booked, the twenty-first is free. He gets Ben, Carol, Dwight, and Luke to go, and the others are supposed to be Ben's chess club. But, Ben takes the school rowdies instead.
Ben has his eye on a girl who is constantly rebuffing. He's planning to ask her out. At the same time, he treats a girl who worships him like dirt. Luke makes a connection with her. He's hesitant to make a move because of Ben but Mike convinces to. When the girl Ben was planning to ask out shoots him down, he decides to ask out the one who follows him, but she's already with Luke and Ben doesn't take it well.
Luke's trucker father comes and tries to reach out to Luke but Luke rebuffs him. When he's about to leave his back goes out so they take him and Mike is incredulous as to if he's really hurt. But Maggie tells him that according to the doctor he is and that if he continues to drive a truck it could get worse. Jason and Ben deliver his load which proves to be no easy task.
Mike proposes to Kate, realizing he wants someone to cook and clean when his mom moves, but she furiously turns him down. Maggie wants to refuse the job since Ben is against moving, but Mike talks to his little brother and they strike a deal.