Kate's latest matchmaking client is a former call-girl who wants to leave that life behind, find real love, and start a real relationship. Meanwhile at the office, her next client is a wife who is suing her husband for being too stingy.

Kate is supposed to be a bridesmaid in her friend Gabrielle's wedding, but when the wedding is suddenly called off, she has to become her lawyer instead.

After some tough love from her best friend Victoria, Kate confronts her ""love"" addiction and tries to set some boundaries between her life and those of her clients. She even tries attending a ""love addict"" support group only to run into Jarred, the romantic book salesman who she just set up with a client named Rachel who had all but given up on love. Kate's resolve to stay professional in matters of the heart is immediately put to the test when one of her seemingly successful matches, Michael and Amy, hits a rough spot and she instinctually runs to the rescue only to find herself in a rather awkward position between the two of them. Meanwhile, in court, Kate faces off against Jerry 's ex-girlfriend, the vicious Sandy in a difficult settlement case.

As Thanksgiving approaches Kate, is facing major family issues both with her client, rapper Master Z, who is desperate to prevent his ex-wife from taking their two sons to Hawaii for the holiday with her new boyfriend and because her mother Liane and Jerry refuse to be in the same room to share a meal. In the spirit of the holidays, Kate is able to negotiate a truce between her parents, although it means sending Nick to Las Vegas to shuttle her father home, while also inviting Master Z and his posse as well as Victoria and her wayward cousin, and her newly single client Lonniman to join the festivities. Meanwhile, Amy apologizes to Kate about shutting her out of her relationship with Michael, but when Kate gets back in, she finds that their relationship is not as perfect as it seems to be and Michael wants out. He decides to cancel on Amy's plans to go to her parent's house for Thanksgiving, and ends up a Kate's house instead. A plan which backfires when Amy decides to change her plans