Kate runs into a former crush at her high-school reunion; Lianne claims to be Jewish after she meets a Jewish man on an Internet dating site; Kate urges a wealthy female client to sign a prenuptial agreement.
A successful fellow matchmaker makes Kate an enticing partnership offer, which forces her to make a major decision regarding her law career; Nick begins having panic attacks after Victoria moves in with him; one of Kate's clients sues her ex for wasting her time.
Adam bribes Lauren, hoping she'll drop the malpractice suit against Kate; the husband of one of Kate's clients returns after several years, claiming he has amnesia; suspicions arise around the identity of the father of Lauren's baby.
Kate is sued by Lauren for malpractice over her divorce case. Also: Adam comes to town and attempts to woo Kate, though she is trying to set him up with Victoria. Also: Kate gets a high-profile client.
A major twist in Lauren's divorce trial opens Kate's eyes to something Michael has been hiding for months. But before she can settle anything with the architect of her dreams, there's the minor matter of helping an Indian woman out of her arranged marriage. Meanwhile, Victoria learns that her stars are aligned with Nick, who seems to be previously engaged with a clingy office temp. Sanjay: Tareq Kabir. Rashmi: Sunita Param. Lauren: Dina Meyer. Michael: David Conrad.
Michael and Kate's efforts to keep their fling under wraps begin to unravel after Lauren (Dina Meyer) pulls out the big guns to get him back. Meanwhile, Serena Lockner (Charisma Carpenter) returns to enlist Kate's help in adopting the perfect child in time for the holidays; and Victoria sees the downside of getting naughty with a department-store Santa. Victoria: Lake Bell. Michael: David Conrad. Nick: James Roday.
Kate's client (Dina Meyer) turns out to be Michael's old flame, casting a chill on what was brewing into a hot new romance for Miss Fox. Meanwhile, a pushy judge hires Kate to find her a man who can withstand her cross-examinations; and a woman comes to the firm for help after her husband strays on a reality TV-show. Michael: David Conrad.
Thanksgiving has Kate's place stuffed to the rafters when she hosts dinner for her feuding parents and a divorced rapper (Romany Malco) who can't be with his kids over the holiday. Good thing there are leftovers, since Veronica, Nick and one of Kate's newly single clients are also on their way. Liane: JoBeth Williams. Lonniman: Reg Rodgers. Nick: James Roday. Veronica: Lake Bell.
Hoping to stay out of her clients' lives, Kate joins a support group for love addicts, but her romance recovery is challenged by Michael's latest woes with Amy. Meanwhile, Miss Fox's courtroom career meets a similar threat in the form of her father's ex (Michelle Lee). Amy: Katherine Lanasa. Michael: David Conrad.
Kate and Sid find it extremely challenging to represent a woman who wants a divorce settlement without having to legally separate from her stingy husband. Kate's latest matchmaking project also requires thinking outside the box because the client is a call girl who desperately wants a real relationship with a respectable guy. Also, Michael's looking for a date to turn heads at a charity dinner.
Kate helps a friend (Amanda Detmer) sue her ex-fiancé for the cost of the wedding he called off at the last minute. But the client-lawyer privileges run dry when Kate starts dating a fellow she met at the couple's shower. Gary: Bradley Cooper. Amy: Katherine Lanasa.
Kate tries to do damage control after undoing the high-school sweethearts who hired her for dates with other mates before tying the knot. But one thing Miss Fox realizes that she's not missing is her ex (David Alan Basche), who asks for a second chance. Meanwhile, a divorce client (Richard Kind) needs the firm's help in getting the truth out of his former wife. Connie: Jenna Fischer. Scott: Eddie Kaye Thomas. Nick: James Roday.
Ignoring her growing fondness for Michael, Kate reluctantly sets him up with a snobby old friend (Charisma Carpenter), while a good-natured chiropractor sets his sights on Miss Fox. In court, the firm defends a man accused of cheating on his wife with the world's hottest nanny ever. Michael: David Conrad. Kate: Alicia Silverstone.
Kate pulls a fast one on Laurel (Melissa Errico) for stringing along two of her top clients, including Michael (David Conrad). In court, the firm represents a slacker who fears his ex had their baby without telling him. Jerry: Ryan O'Neal. Nick: James Roday.
Ryan's constant criticism has Kate fearing that her own love life is as broken as those she's trying to fix, while Sid (Ryan O'Neal) bristles at Kate using his high-powered practice for her very impractical hobby. Michael: David Conrad. Russell: William Ragsdale. Chelsea: Maria Thayer. Ryan: David Alan Basche.