After a chance encounter with childhood sweetheart Josh Chan, Rebecca Bunch uproots her life and moves across the country, hoping to find happiness in his arms. As Rebecca settles in, new coworker Paula begins meddling in her business.
Rebecca meets Josh's friends and goes to great lengths to bond with his girlfriend, Valencia. Meanwhile, Paula begins devising schemes to get Josh and Rebecca together; and Greg struggles with his feelings for Rebecca.
In an attempt to get her mind off of Josh, Rebecca flirts with notions of having sex with a stranger and settling for Greg. Meanwhile, Heather studies Rebecca for her psychology class; and Josh tries to land a new job.
After Rebecca and Greg's disastrous date, Greg accuses her of being a terrible person in front of Josh. Rebecca takes drastic measures to prove she is a good person, which includes helping Darryl with his messy divorce.
Paula keeps Rebecca under video surveillance when she's invited to Josh's family's Thanksgiving. Meanwhile, Greg makes plans to quit his job and go back to school, but a family emergency interferes.
When Rebecca decides to self-medicate, she begins having hallucinations of Dr. Phil. Meanwhile, Paula contemplates having an affair with a distinguished client; and Josh's friends help him assemble a table for Valencia.
Stress levels skyrocket when Rebecca's passive-aggressive mother arrives for Hanukkah. Meanwhile, Heather and Greg spend an awkward Christmas at his mother's house; and Josh attempts to recapture his former dance glory.
