Kate Fox, a divorce attorney, is rushing through traffic to make it to her friends' wedding. At the church, her boyfriend Brian scolds her for being late. Kate isn't pleased about his criticism because she's had a rough day. At the wedding reception, the bride toasts Kate for setting them up. In fact, they are now the third couple for whom Kate has been a matchmaker. After hearing this, Kate is approached by Richard, a cancer researcher who has already given up on hope of finding a mate. The wedding photographer also takes her picture along with the happy couple.
The following morning Kate is having a coffee at a local coffee house with her best friend Victoria. Victoria shows her the day's paper: on the wedding column there's a short story — and a photo — about Kate's abilities as a matchmaker. Kate hopes her father will not find out about this. She fears it would ruin the law firm's — and her father's — reputation as ruthless divorce attorneys if she's seen as a romantic softie. As she leaves the coffee house, Kate accidentally sets up another couple by offering them a table. Maybe there's some truth to the newspaper story after all? At the office, receptionist Claire tells her that she has 12 messages waiting from people looking for the "marriage broker".
Kate's co-worker and her father's younger partner, Nick, a slightly cocky young man, says he's willing to take on some of Kate's single friends. Kate's not impressed. She and her father meet with a client. Russell Dixon is looking to divorce his wife, Jolene, because ever since her clothing business has taken off, their marriage has been crumbling. Jerry Fox suggests that while Mrs. Dixon is out of town, Mr. Dixon empty out his bank account and meet with some of the best divorce lawyers in town to bar them from having any contact with his wife. Kate is not happy about her father's questionable ethics and confronts him after the meeting.
Kate and her psychiatrist boyfriend Brian meet her mother Lianne for drinks and dinner at the restaurant she's performing as a singer. Lianne is worried that Kate is exhausting herself by working too much. Brian has a solution for this: he surprises her with plane tickets to Maui. Kate is taken by the gesture but says she can't just leave her work on such a short notice. Late at night, Kate decides to call Richard, the cancer researcher. She wants to set him up for a date after all. He's not ready to come out of his "dating retirement" but Kate convinces him to try it out.
The following morning, Kate is getting ready to leave for court. Her father says he can't make it to the hearing so he's sending Nick in his stead. Kate hopes her father would let her show that she can make it on her own. She doesn't want people to think that she only got the job because it's her father's firm. She also mentions meeting with her mom, Jerry's ex-wife, and hopes that she could spend more time with her father. Jerry agrees and they set up a dinner date that night.
Kate has asked receptionist Claire to contact a few of the women who called for her matchmaking services to see if she can find a suitable date for Richard. She meets them at the Sunset Lounge, an open-air bar where Victoria works as a bartender. None of the candidates seem very promising, except Laurel, a TV producer. Victoria thinks that she's too gorgeous for Richard but Kate thinks they're a good match and sets them up for a date.
She meets Jerry at a restaurant for dinner. He tells her Brian called to ask if Kate could take some time off from work for their vacation. Kate is a surprised by Brian's audacity since she told him now is not a good time for her to go to Hawaii. Jerry tells her to loosen up and live a little. Kate agrees; after all, she came here tonight to have a good time with her father. But it seems that's not what Jerry had in mind. He has "accidentally" invited a date — whom he insists is just a client — to join them for dinner. Kate quickly excuses herself, pretending that she still has some work to do.
The following day Kate meets with another client, Chelsea Greer, who is getting married the next weekend. Her boyfriend Bradley comes from a rich family and has suddenly asked her to sign a pre-nupt. She's willing to agree to the pre-nupt but Kate thinks otherwise. Chelsea obviously hasn't read the document. To Nick she reads aloud the conditions: for any pound of weight Chelsea gains during their marriage, she's agreeing to a $10.000 reduction in marital property in the case they ever get divorced. Nick, ever the cynic, is impressed by the pre-nupt but Kate is sorry that she has to burst the girl's bubble by showing how shallow her boyfriend is.
Claire announces that Laurel has come to meet Kate. Fearing the worst, Kate quickly calls Richard to ask how their date went. Richard thinks it went well and she really liked Laurel. But Laurel tells it was a disaster and she is hoping Kate could set her up with someone else instead. Kate tells her that there isn't anyone else; it was just a one time thing to help Richard. But Laurel insists: she's having her 10-year high school reunion and she doesn't want it to look like she can't find a husband. Kate agrees to work something out.
Kate and Jerry, representing Russell Dixon, meet with Jolene Dixon and her lawyer. She wants to have a quick settlement and offers her husband $50.000 of her pre-marital assets if she gets full custody of the couple's dog, Pepper. But Russell says the dog is everything to him. He's not willing to give him up for $50.000 — instead, he wants half of her pre-marital assets of over $1 million. They settle for $100.000 which will be finalized in court.
At night, Victoria and Kate hit the bars to scout some would-be dates for Laurel. Kate introduces herself to Michael, a very cute architect, but he isn't interested in being set up with a random woman. Kate leaves him her card anyway.
The next morning, Kate and Chelsea meet with her boyfriend Bradley and his family lawyer. She tells them the entire weight gain condition is unacceptable. Chelsea thinks that Kate is taking the whole thing too seriously but Kate tells her she shouldn't be marrying a guy who only thinks of her as a purchase.
Arriving at the court house, Kate gets a call from Brian who is planning their vacation in Hawaii. He emails Kate some information about the local restaurants and asks her to take a look at them. When Kate tells him she's busy, Brian complains about Kate not taking part in the planning. Just outside the court house, Kate spots Russell yelling at the top of his lungs to Pepper the dog. She realizes that he has just used the dog as a bargaining tool to get a share of his wife's money. When the divorce is finalized, Jolene runs to the bathroom to have a cry. Kate comes in after her and tries to console her by setting her up for a date, but she isn't too keen on receiving advice from her husband's attorney. Jerry sees this and scolds Kate for giving women advice about their marriages. It turns out that Chelsea has changed her mind and is not agreeing with the pre-nupt after all, and now the Kesslers are suing the firm for $20.000 in damages for the reservations at the Four Seasons Hotel. Kate and Jerry get into a huge fight about how to run the company. Jerry demands that Kate agree to his ways — or else she can leave the firm.
The next morning Kate finds Chelsea and asks her to reconsider and compromise. She doesn't have to agree to Bradley's pre-nupt but she can come up with her own draft. When she drops the revised draft at Bradley's office, she learns that the two met at a Jenny Craig weight loss program. The weight gain condition in the pre-nupt was drafted as an incentive for the both of them to keep their current weight. Kate advices him to take a look at the new draft.
Laurel calls Kate again: she is desperate to find someone because her high school reunion is the following day. With no one else to turn to, Kate sets her up with Nick. That night, Richard is having a terrible date with one of Kate's acquaintances from law school. Laurel and Nick's date isn't going any better when he insults her by making comments about "desperate women".
The following morning Kate is woken up by Brian calling to invite her to a pre-vacation breakfast. But she can't make it because she has a meeting. Besides, she hasn't even packed yet. Brian instructs her to pack lightly because he hates waiting at the luggage check-out.
Kate meets Richard and his Great Dane in the park. He's had enough with the disappointments and is willing to give up again, but Kate tells him that one day he will find his soul mate. Then she spots that he is wearing an Outgear sweat suit — the very same brand of clothing that Jolene Dixon started. Sneakily, Kate tricks her into going out with Richard by setting him and his dog up as a play date for Pepper.
Brian comes to pick up Kate for the airport. In a hurry to pack, Kate has forgotten everything about his instructions to take just carry-on bags and has packed a huge luggage that they have to declare. Brian starts to bitch about this the second they get into the car. Kate's had enough. She's fed up with Brian's constant complaining and him trying to change Kate to someone he really wants to be with. She gets out of the car and breaks up with Brian right there on the driveway. Fighting back tears Kate goes back inside but she can't help but feel a little relieved. Brian speeds away.
Kate meets Laurel who tells her how awful it was to go to the high school reunion alone. She's even willing to pay Kate $1.000 is she can find her someone. Kate agrees to help her. Since the vacation is canceled, Kate goes to the office instead. Jerry comes in to tell that the Kesslers agreed to Chelsea's revised pre-nupt... and to apologize. He doesn't want Kate to leave the company. Kate doesn't want to leave either, but she still thinks that helping the women get over a devastating divorce is, in a way, part of her job. Jerry agrees.
After work, Kate hangs out with Victoria at the Sunset Lounge, being miserable over her broken relationship. Out of blue, Michael, the cute architect, shows up looking for Kate. It turns out he's been working up the nerve to call her for the past two days. He asks if the TV producer Kate's was talking about is still available. She is... but Kate thinks she can find him a better match. And during the weekend, Chelsea and Russell get married, and Richard, Jolene and their dogs get together for a play date in the park. It looks like Kate's instincts have been right again.