Carol has a new boyfriend and their relationship interferes with her time at work. She thinks about moving in with him to be together more. Howard has another girlfriend and is worried about keeping her.
Bob makes plans with Jerry to watch Monday Night Football at Bob's place. Emily is upset because she feels left out. They argue the next night about his ignoring her. Since they do not go to bed angry, they stay up all night.
Bob feels like everyone wants his time and that he has no time to himself. He decides to stay at a hotel for a night for the solitude. Everyone thinks he is leaving Emily. Meanwhile, Emily tries to get a book for the school library.
Jerry talks to Bob about not being happy in life, and then decides he wants to see Bob professionally. When Bob presents the bill to Jerry, he is shocked to see how much he is charged. The bill causes problems in their friendship.
It's Christmas time and Bob's therapy group is not a happy bunch. Bob invites his patients to share Christmas Eve with him and Emily. Bob worries about what to give Emily for a gift.
Bob & Emily decide to go on a weekend trip and pick a nearby ski resort. Instead of a relaxing time together, the only other guests share their bathroom and want to share time with them.
Carol turns 29 and feels unfulfilled. She quits her job to explore other options. Carol joins one of Bob's group sessions and as the group explores Carol's feelings, Bob is asked how he feels. The group treats him as just another member.
Emily gets Bob a really expensive watch for his birthday. When he finds out how much it costs, he is shocked that she would spend that much money on one small gift.
Howard's sister Debbie, visits, and he wants to remove all signs of his dating habits. He thinks she is young and impressionable. Debbie arrives and Emily sets her up on a date. Howard turns over protective.
Emily is offered a job with the school, and Bob tells her she should take the job if she wants it. She takes the job and Bob has a hard time adjusting to the differences.
Bob helps a Cubs pitcher get out of a slump when playing baseball. The pitcher does well in the next game and credits it to Bob. Hearing this, another player, the catcher, goes to Bob for help.
Bob's therapy group had a great session and Bob is reluctant to take a vacation during this time. Bob & Emily have a 63-day cruise scheduled and he thinks it is too long to be away. His patients encourage him to go.