- A lawyer decides that she's used too much like a nanny by her boss, so she walks out on him.
- Harvard educated lawyer Lucy Kelson, following in the footsteps of her lawyer parents, uses her career for social activism. She hides any sense of femininity behind her work. George Wade is the suave public face of the Manhattan-based Wade Corporation, a development firm that Lucy routinely opposes and whose true head is George's profit-oriented brother, Howard Wade. George, who has a reputation as a lady's man, has had as his legal counsel a series of beautiful female lawyers with questionable credentials, they who have more primarily acted as his casual sex partners. Needing a real lawyer, he offers Lucy the job of his legal counsel on a chance meeting. Despite warnings from her parents in working for the "enemy", Lucy, who has no intention of being the latest in his bed partners, accepts the job as she feels she can do more good from the inside, and as George, as part of the job offer, promises not to demolish a community center in a heritage building as part of a development project near her childhood Coney Island home where her parents still live. Although Lucy is able to effect the type of change she wanted from this position, she finds she cannot deal with George's expectations of her, namely being his primary confidante and advisor at all hours of the day and night, mostly about issues she considers frivolous. As such, she gives him two weeks notice, although she promises to help George find her replacement. As Lucy begins to review resumes, George himself unilaterally decides to hire June Carver, a fellow Harvardite, but who seems to have her sights set on George as both a boss and personal partner. As June begins to replace Lucy in seemingly all aspects of George's life, Lucy begins to realize that she herself has fallen for George. However, Lucy's feelings for George and her attempts to re-ingratiate herself into George's life are placed into jeopardy when she learns of a Wade Corporation decision against her basic sensibilities.—Huggo
- Lucy Kelson, the brilliant but insecure lawyer with a sharp, strategic mind, is working as a Chief Counsel for the Wade Corporation: one of New York City's most important commercial real estate developers. As a result, she can't get much sleep, and as if that weren't enough, she also has a chronic ulcer. Of course, it's not the job that's getting to her; it's her millionaire boss, George Wade. Handsome, charming, and, irrefutably, self-centred, George treats Lucy more like his nanny than a well-trained Harvard Law graduate, and what's even more impressive, he can barely choose a tie without her help. Now, after one long year of calling the shots--pretty much on everything, from his clothes to his divorce settlements--Lucy Kelson is finally calling it quits. But, Wade is given two weeks notice. Is it ever too late to say "I love you"?—Nick Riganas
- LUCY Kelson (Sandra Bullock) is protesting the demolition of a 75 year old building that she says is a landmark. Lucy is arguing with a construction worker who is telling her to move so the crew can proceed with the demolition. Lucy, along with her two friends Meryl and Tom, lay down in the street hoping to prevent the demolition. While laying there, Tom proposes to Meryl who says yes. The police show up and arrest all three.
Lucy and her friends are bailed out by Lucy's parents, Larry (Robert Klein) and Ruth Kelson (Dana Ivey). Lucy thanks her parents but is dismayed when she finds out the building was still demolished after they were arrested. Her parents tell her that is what the Wade corporation does, and the company even has plans to build condos near their house and knock down the local community center.
Lucy goes home to the apartment she shares with her parents. She orders an insane amount of Chinese food considering it's only for one person as she is a big stress eater and reads a magazine article about George Wade and the Wade Corporation while eating.
GEORGE Wade (Hugh Grant) is receiving a Man of the Year award due to millions donated to a hospital by the Wade corporation. George gives and acceptance speech and an interview with the press. George mingles with various people at the event when he is approached by his driver Tony who tells George that George's brother wants to see him tonight. George arrives at his brother's house where he exchanges pleasantries with his sister-in-law and the housekeeper before going to see his brother in the gym.
HOWARD Wade (David Haig) tells George about deals the company lost because of the incompetence of the legal counsel George has hired. Apparently, this latest attorney hired by George is just another in a line of attractive women with law degrees from mediocre schools. Howard tells George to hire someone from Harvard, Yale, etc.
The next day Lucy is approaching the Wade building. George is walking out talking to an attractive female attorney he just interviewed. After the two part ways, Lucy approaches and introduces herself to George as he is walking to his car. Lucy mentions she is an attorney which prompts George to ask her if she has ever heard of Saint-Tropez Law School, presumably the law school attended by George's recent interview. Lucy says no. George asks Lucy where she attended law school, and Lucy tells him Harvard. This intrigues George who asks for her background. Lucy tells him about the legal aid organizations for which she has worked. George comments that working for those organizations can't pay much, and Lucy tells him she isn't very interested in money. George laughs but then recognizes her name as being the attorney who protests his company as well as other similar companies. George realizes Lucy isn't there for a job. Lucy tells George she is there representing the Coney Island Community Center. Lucy tells George about all the activities the community center has and how important it is to the neighborhood. George tells her that another company has the inside track for the contract. Lucy tells him her parents know a local politician involved in the process who will guarantee the contract to Wade if Wade agrees to keep the community center. NORMAN from Wade runs out to speak with George telling him about an appointment coming up very soon as well as needing a quote for an article. George starts making up a quote prompting Lucy to piggyback off what he is saying to promote the community center. George uses her words to finish the quote. George has Lucy get into his limousine with him since he is running late for an appointment. George offers Lucy a deal. If Lucy accepts the job as Wade's chief counsel, George will promise to keep the community center as well as allow her to direct all of Wade's charitable endeavors. Lucy says she is unsure, and George tells her to think about it.
Lucy walks along the boardwalk outside the community center while thinking about the offer. Lucy eats at a restaurant with her parents. Her mother tells he she can't work for Wade, but Lucy points out how it's the only way to save the community center as well as the other resources she will have to do good.
Lucy takes the job. Two weeks later, Lucy stops to talk to George about a Wade project. George asks Lucy her opinion about which of two envelopes he should use for his new personal stationary. Since the two look identical, Lucy licks both and picks the better tasting one. George says he has already asked 30 people, and Lucy was the only person to come up with that answer. George is impressed and says he is going to get Lucy a bigger office.
Six months later, George has Lucy with him helping him pick out a mattress. Four months later, Lucy is sleeping when her phone rings. George is calling from the bar at 2:15 am. Lucy is annoyed and tells George to put whatever girl he is talking to at the bar on the phone. Lucy tells the girl a bunch of things to get her to leave George and go home. Lucy then tells George he should be getting sleep since they have a meeting about his divorce in the morning.
The next morning, Lucy is sitting in a conference room with George's soon to be ex-wife LAUREN and her attorney, BUZZ, while waiting for George, who is late. George finally shows up. Buzz says he wants to discuss the terms of the settlement. Lucy tells him the terms have already been set since there is a pre-nuptial agreement. Buzz says that George's infidelity in the marriage can warrant change to the terms. Lucy tells Buzz that Lauren cheated as well during the marriage with the company accountant. Lucy says they will not agree to pay any additional alimony, but George cuts her off saying they will pay it as long as she signs a form releasing him from any further commitments. Lauren lashes out calling Lucy a bimbo and throws water on her.
Lucy and George walk back to the Wade office. Lucy is annoyed with George for agreeing to pay the additional alimony. George tells Lucy Lauren would have kept fighting for it, and George wanted it to be done and over with. While walking past what appears to be a needy person holding a coffee cup, Lucy throws change in the coffee cup not realizing the cup is actually filled with coffee and not for donations. The needy man flips out on Lucy. George pulls her away and says he needs her help on something important. The important thing is George shopping for clothes. Lucy is annoyed with George for having her help out with non-legal mundane tasks and leaves the store leaving George behind.
Two months later, Lucy is the Maid of Honor in Meryl and Tom's wedding. During the ceremony, Lucy's cell phone rings. On her phone is a message from George that says, "EMERGENCY Come ASAP **GEORGE**." Much to Meryl's shock, Lucy runs out of the church and hails a taxi to the hotel George lives in. Lucy tries to call George on the way to find out what's wrong, but George doesn't answer. Lucy enters George's penthouse, and George yells for her to come into his closet. George's emergency is that he's judging the Miss New York contest in an hour and doesn't know what to wear. Lucy is horrified to discover George called her out of a wedding to pick out a suit. George didn't know she was in a wedding and seems surprised she left the wedding. Lucy points out that George said it was an emergency and reminds him she has previously informed him as to what constitutes an emergency. While picking out George's outfit for him, Lucy reminds George this current situation doesn't count as an emergency as well as previous situations George similarly summoned her including calling in the middle of the night or interrupting her "lady doctor" visit for similarly non-emergency reasons. Lucy is fed up and tells George she is quitting and to consider this her two weeks notice. George seems distraught and starts lashing out calling Lucy ungrateful and pointing out she left her cell phone on because she craves excitement and emergencies. George points out that before Lucy came into his life, he was capable of making all kinds of decisions, but now he needs her opinion on everything. Lucy leaves in disgust.
Lucy tells her boyfriend Ansel on the phone about quitting, but the conversation is cut short as Ansel is shipping out on some new Green Peace mission. Lucy goes on three job interviews. All three interviewers tell Lucy they can't hire her because George doesn't want them to. Lucy goes into George's office who is currently getting massaged by two masseuses. Lucy yells at George about him calling other places preventing her from getting another job, George points out that Lucy has a contract that says she will work for Wade until at least the completion of the Island Towers project, which is the initial project Lucy got Wade in order to save the community center. The contact, which was drafted by Lucy, says that George can stop her from working anywhere else until the project is completed. Lucy's parents review the contract but can't find any loopholes in it allowing Lucy to break or void the contract. Lucy's dad offhandedly mentions there is nothing Lucy can do short of going in and deliberately trying to get fired. This catches Lucy's attention who appears to have an idea.
Lucy goes to work the next day deliberately trying to get fired. Lucy shows up late to a meeting with George and Howard while chewing gum. Lucy rudely bumps into Howard, insults Howard's children in a picture, spits out her gum on the floor which is then stepped on by Howard, and pretends to be clueless when asked for her opinion for ideas. George takes Lucy out of the meeting telling her he knows what she is trying to do, and it is not going to work. Having now stopped outside the Men's bathroom, Lucy grabs George and takes him in the bathroom to talk. Lucy explains the negative impact George has on her life. George tries to promise to be better, but Lucy says he won't be and George agrees. George agrees to let her leave after she finds a replacement. Lucy thanks George and hugs him. Her earring falls out on the ground. Lucy bends down to pick it up, but while standing back up, her hair gets caught in George's belt. While George and Lucy are trying to get Lucy's hair uncaught, Howard walks in to see Lucy squatting down in front of George appearing as if she is pleasuring him.
Lucy and George do a photo shoot to promote the project at the site of the Island Towers project. Lucy walks over to say hi to her parents Larry and Ruth who have come to say hi since the site is right by their house. George comes over and says hi. They all go back to Larry and Ruth's apartment for cake. Lucy and George go up to the roof and talk while eating cake. Lucy talks about the difficulties of her mother having such high expectations whereas George contrasts it saying it's better than people having no expectations of you.
Lucy and George conduct the first interview for Lucy's replacement. George congratulates the interviewee, who is a heavier woman, on being pregnant, but she is not pregnant. Lucy and George go to lunch after the interview. George suggests Lucy conducts the interviews without him moving forward. While Lucy is listing some names of possible candidates including men, George tells her it has to be a woman because it will annoy Howard. Their closeness is obvious as they get the same salad and immediately start picking off things they know the other person doesn't like but they do.
George walks into Lucy's office to ask him about his outfit for a tennis charity event later that evening. Lucy is obviously upset and angrily stapling papers telling George she just had a fight and broke up with Ansel. George cancels his plans to attend the charity event and takes Lucy out on his yacht to cheer her up. Lucy gets drunk and starts talking about how she always drives men away. George theorizes that it's because Lucy doesn't really like the men she's dated. Lucy says that doesn't make sense because they have all the same political views and ideologies. Lucy says George may be right, but she's never been very passionate about anyone. Lucy passes out. George carries Lucy into her apartment which is in the same hotel that George owns and lives in.
Lucy is hung over the next morning drinking coffee outside when George approaches her. She apologizes for the previous night and checks with him to make sure they didn't have sex or anything which George reassures her they didn't.
Lucy is in the break room at work drinking coffee when Norman comes in scaring her causing her to spill coffee on her shirt. Norman says an attorney from Harvard is there to see Lucy. Lucy looks at her resume remembering it noting that she didn't have a strong background in property law which is presumably why Lucy had not set up an interview with her. Norman says she is down from Boston and only wants five minutes, and Lucy agrees to meet with her. Norman brings her to Lucy's office. JUNE Carver (Alicia Witt) introduces herself to Lucy. June flatters Lucy telling her she is a legend at Harvard Law School as previous editor of the Law Review and mentions articles written by Lucy while there. June admits not having a strong background in property, but mentions how Lucy did not either when she graduated from Harvard and has done so well. June mentions she was impressed by a quote by George Wade about the challenges of urban development in an article she had read. June reads the quote which is the quote Lucy and George came up with during their first meeting outside the Wade building earlier in the movie. As June finishes reading the quote, George walks in. George mentions that Lucy actually wrote the quote. Norman then comes in telling Lucy she is needed on a call from the Zoning Commission. Lucy tells June they should set up a proper interview for tomorrow, but George volunteers to finish the interview. Lucy seems a little disheveled about George wanting to finish the interview, possibly since June is very attractive.
That night, George and Lucy are at the Mets game. Lucy asks George what he thinks of June. George mentions that he likes her, that June and him went out for a drink and talked for hours, and he even got her a room to stay at the hotel since she didn't have anywhere to stay. George also mentions he invited June to the company tennis outing. A foul ball is popped up and heads right for Lucy and George who are in front row seats. Mets catcher Mike Piazza starts running over to try and make the catch. Lucy is waving her hands above her head afraid for the ball to hit her and ends up blocking Piazza from making the catch. The whole stadium starts booing Lucy who is now being shown on stadium big screen.
At the company tennis outing, George and June are playing a doubles match against Lucy and Norman. Lucy and June seem to be particularly competitive against each other. This eventually leads to June hitting an overhead shot that hits Lucy right in the head. Lucy sits on the side of the courts eating while watching George and June flirting with each other.
While George and Lucy are driving back from the outing, Lucy's stomach starts bothering her since she ate too much. As George and Lucy are stuck in traffic on the bridge, Lucy realizes she really needs a bathroom. George gets Lucy out of the car and runs with her to an RV also on the bridge. George offers the family in the RV $100 to let Lucy use their bathroom. While Lucy is still in the bathroom, traffic starts moving and the RV drives by Lucy's parked car. Lucy and George are dropped off at a shopping center parking lot after they are off the bridge. Lucy asks George where the car is, and he responds it has probably been towed by now. George takes out his cell phone and says he'll call for a lift. A Wade helicopter lands in the parking lot and picks them up to fly them back to the office.
At the office, George is in the break room when June comes in and starts talking with him. June asks about the big charity benefit everyone is going to that night almost kind of fishing for an invite. George invites June to the benefit. June drops something off to Lucy in her office. Lucy tries to give her something else to do, but June mentions she may not have time as she has to get ready for the benefit since George invited her. Lucy seems annoyed about George inviting June. Lucy gives George documents to sign while leaving the office and tells George she doesn't need a ride to the benefit when George mentions picking her up.
George is in the back of his car when he receives a call from Howard. Howard says he got the new costs estimate for Island Towers. Since costs are going up so much, they are going to have to knock down the community center since it will be so much cheaper to do so. George argues with Howard saying they only got the project because they promised to keep the community center. Howard says they never promised to keep the community center; they only said they intended to keep it. George goes over Howard's house to discuss the matter. Howard tells George that George needs to give a speech at the groundbreaking event. George refuses because he doesn't agree with the company knocking down the community center. Howard tells George he will do it or he will be fired.
George, June, and Tony walk into the charity benefit. They are dressed a little silly since the benefit is for a children's charity with George wearing a tie 3-4x bigger than normal. They are greeted by Howard and his wife. George goes to get June a drink. George looks across the benefit and notices Lucy looking very nice all dressed up. George and Lucy say hi to each other. George is taken aback at how Lucy looks all dressed up. Lucy says she completes the outfit by putting on a clown nose. June comes up and says hi. June mentions that Howard wants June to revise the Island Towers proposal now that they are tearing down the community center and could really use Lucy's help. Lucy is shocked and asks to speak to George in private. George and Lucy have an argument. George says he argued with Howard to try and keep the community center, and it doesn't matter because Lucy is quitting. Lucy says she is disappointed with George for not trying to be the person he could be, and this is the first time in a year that she really doesn't like who he is. Lucy storms off.
George and June get back to the hotel and get into the elevator. June starts kissing George, and instead of getting off on the floor to her room, they go up to George's penthouse. June sees a chess board and suggests they play strip chess. Lucy walks into the hotel and takes the elevator up to George's place. Lucy walks in calling out for George when June pops in from the kitchen only wearing a bra and slip. George then comes out without any pants on and stops when he sees Lucy. George says they are just playing chess, and Lucy says it's fine and she's about to go have sex herself. Lucy leaves and goes to Meryl's place to return her the shoes she borrowed. Lucy tries to leave right after, but Meryl stops Lucy to talk and console her as Lucy is upset.
The next day at the office there is a farewell party for Lucy. June stops by to say goodbye to Lucy and apologizes for last night. June jokes about Lucy stealing the company's stapler, and Lucy laughs when June talks about keeping her personal and professional life separate. This leads to a physical altercation between the two causing the need for them to be separated. George takes Lucy into another room. George tries to talk to Lucy about the situation while Lucy just keeps asking George if he is still planning to knock down the community center. The two argue with George telling Lucy she's alone because no one is as perfect as she is and not everyone wants to be preached to all the time.
Lucy is back living with her parents in the apartment and orders Chinese food. At the groundbreaking event for Island Towers, George starts to give his speech. Lucy and her father Larry are having breakfast and talking. Lucy is discouraged about the situation. Larry tells her she can't give up and that people can change. Lucy says she's worried that people can't change. Larry points out how he's eating something healthy right now that he hates for her mother, so people can change. Lucy says bye and goes to work at Legal Aid.
Lucy is at work talking to a woman about helping prevent her from being evicted. She goes downstairs to get forms. George walks in the front door. Lucy comes back upstairs and George says hi. Lucy says she's busy. George says he wants to read her his speech from the groundbreaking event and get her opinion on it. George reads his speech including that Wade is going to keep the community center and not knock it down since they promised the community. George also tells Lucy he didn't sleep with June. Lucy starts to tear up, but she says she has to get back to work. George leaves. After thinking about it, Lucy runs outside after George. Lucy runs into George's arms. Lucy starts rambling, so George stops her and tells her he loves her. Lucy says she loves him too. George mentions he has resigned from his job. The two kiss. Back at Lucy's apartment, Lucy is on the phone ordering Chinese food while George jokes about how small the apartment is. The end.
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