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Jake and Bob misinterpret one of Chris's phone conversations and assume that she and John are sleeping together. At the office, John tries to persuade a promiscuous teen to use condoms.
Margaret looks back 10 years to her first meeting with John. She recalls persuading him to hire her and keep his practice open instead of closing shop and returning to Boston. At the diner, Bob hides from an angry tenant who wants him to fix a clogged drain.
John's former college roommate at Harvard visits to seek forgiveness for past offenses, but John refuses to pardon his old friend. Meanwhile, at the diner, Bob becomes convinced that he is going to die soon; and at the office Linda accuses Margaret of having an affair.