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.
After Jonah was struggling to come up with rent, Riley took a modeling job with WPK Public Relations once a jeans designer wanted to use her in his ad because of her girl-next-door appearance. She and Jo Reynolds, the photographer, did not hit it off to the point where she stormed off the shoot. Her real untrusting feelings towards Ella Simms came to the surface and they argued after her exit.
After Ella created a fake bio for her involving growing up in a ghetto and battling gang violence, Riley spilled the beans to the press, refusing to play along with her charade. Amanda Woodward, however, outraged at the display, called Riley's employer and told them she used sick days to moonlight, which was against the rules. Riley lost her job as a result.
After Auggie left, Riley began dating new tenant Drew Pragin, which eventually made Jonah jealous.