Riley Richmond was a first-grade teacher and the daughter of a Supreme Court attorney and an editor for the Boston Globe. At the beginning of the series, she was living with her boyfriend Jonah Miller, who proposed to her after their five-year relationship. Riley was hesitant to accept because she was intimidated, but agreed to marry Jonah. Throughout the whole first half of the season, Jonah and Riley quarreled constantly, eventually breaking off their engagement by mid-season. She also had mixed feelings for Auggie Kirkpatrick.
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