Lisa (Reese Witherspoon) is a member of the USA Olympic softball team. A college star and Olympic athlete, she is now 31, and despite recommendations of the team and assistant coaches, is being cut from the team by the new coach. He won’t tell her the bad news until he posts the team roster online in a few weeks.
While at practice, Lisa’s cell phone rings, and it is George Madison (Paul Rudd). A teammate of hers gave him her phone number to call for a date. He calls to say that his casual relationship just got more committed, and he won’t be asking her to dinner. She thinks this is a bit strange, but laughs and smiles. George’s girlfriend is a professor who makes her career her priority. George is served papers when he is at work: there is an investigation of his company for securities fraud of their overseas division. His father (Jack Nicholsen) is the President of the company; he started it years ago and it is a successful international company. He briefs George about the charges and their corporate position on the case. George’s secretary, Annie, is pregnant, and very stressed at this meeting, and yet she doesn’t say anything. George is told that he needs to find legal representation, and that the Board can’t fund it. George’s girlfriend tells him that while she will be there for him when the case is over, that for now, they need to push “the pause button” on their relationship, and leaves him.
George goes home, and meticulously makes himself an elaborate Bloody Mary. Later, we see the kitchen in shambles and he is drinking straight alcohol. He sings to himself, and calls Lisa. He tells her he is now available and would like to take her out. She reluctantly agrees, and they decide to meet for a casual dinner.
Before dinner, Lisa gets a text and missed call: she checks the team website and sees she isn’t on the roster, and has been cut. The entire team and coaches come over and talk to her. She nearly forgets her dinner date with George, and leaves in a hurry to go. George has just literally run away from his father, who was going to give him bad news, and he didn’t want to hear it before his date, and ran down the street. She sees him at the restaurant, and his head is in his hands. He is thinking about the possible indictment on him, and makes bad conversation and a poor impression. Lisa snaps at him and tells him that they are going to free themselves from the expectation of conversation and have a SILENT dinner. They eat in complete silence, and after dinner, George is happier, not having to explain or think about his worries. He thinks that Lisa is strong and beautiful, and quite possibly a girl to date. She is relieved the date is over and leaves, not looking back.
Lisa is dating Mattie Owen Wilson), a pitcher for the Washington Nationals. He is self-absorbed, and shallow, and since Lisa isn’t looking for a boyfriend, she treats it as a casual relationship. One night after a date, she has to decide if she is going to “see his apartment”, and does. She spends the night, and in the morning, Mattie makes her a smoothie and wants her to gush over the fantastic sex they had. She begins to dress to leave, and he takes her in the master bathroom where he explains she doesn’t have to wear her dress homeshe is shown a closet full of pink Nationals sweat suits, in various sizes. She is appalled that he is so tacky and sleazy and walks out angry…then turns, and talks to him. She realizes she has different expectations, and apologizes to him. She decides that all she needs right now is a light, casual relationship, with sex, and is ok with Mattie.
George meets with an attorney; he is told that it will cost him $300k for a retainer to start, and another $300k in escrow. George will have to sell everything to pay for this, including his apartment.
Lisa visits a therapist, to talk about her stress and future, then turns to leave and can’t do it. She does ask the therapist one vague question: if he could tell one thing to someone in general, to help them with problems in general, what would it be? His answer: Find the thing you want most, and ask for it. She replies that both of those are hard things and he tells her she is stronger than she thinks and can do hard things. She ponders this and leaves, and joins Mattie at a BBQ at a player’s apartment. She finally asks him why he never asks anything about her or her life, and he stops to listen for the first time. They leave, and she talks about her situation. Mattie listens, but not reallymostly he is just feigning interest. She spends the night, and tells him that if he should hear her crying in the night, to ignore her and not ask if he can help. He says he prefers it that way.
During a baseball game the next day, Mattie asks the guys on the team how he would know if what he feels for a girl is love or not, and one teammate answers that his sure way to know is that he wears a condom with the other girls he sees at the same time. Mattie stops…and realizes he is in love. Later, he calls Lisa and asks her to move in with him. She decides to do it, and sublets her apartment and moves in.
Annie visit George in his new, tiny apartment, and brings lots of homemade food for him, and stocks his refrigerator. She was forced to sign a non-disclosure agreement at work, and is forbidden to talk to George about work or the indictment. He is ok with that, and doesn’t want her to jeopardize her job, especially since she is pregnant and needs the money and insurance. She tells him she KNOWS things, and wants him to guess, and she can just nod without actually telling him anything. George refuses, as he knows the only thing he has in his favor is that he is totally honest and has done everything legally and truthfully, and clings to that thought to survive. She is distressed that she can’t warn or tip him off, and finally gives up trying.
George has to meet his father at his luxury apartment for more discussion on the investigation. He gets more bad news, and after leaving, bumps into Lisa in the elevator. She invites him up to her apartment, and he carries her groceries. Inside, Mattie comes out and she introduces him to George. Mattie is angry that she invited some dude over without clearing it with him first. Lisa pulls him aside and vents on him as to why she would have to clear it with him. He answers that it is “his place”. Lisa is shocked by his attitude and selfishness and overall rude behavior, and packs up and moves out. Mattie turns to George and remarks that he probably just blew it, and George replies that from his perspective, he didn’t.
George invites her over and they take the bus to his apartment. She asks him to get her some Guinness, and he happily does. He makes her one of his specialty drinks, and they drink and talk, and laugh. They both open up about their problems, and George is clearly in love with her. She tells him that she doesn’t know what to do with her life: most of her teammates want to get married and have a baby when their softball careers end, but she doesn’t feel that way, and wonders if she has what it takes for the regular life plans that everyone else has. George explains about his troubles, and they continue to drink and get drunk, and talk and bond. Much later, her phone rings, and it is Mattie, who apologizes and wants her back. She accepts his apology, and sadly, George calls a taxi for her. They agree to be friends and hang out sometime. As she leaves, he is sad.
Making a visit to his dad, George tells him he needs to know if he did ithis dad explains that bribing officials is how business is done in other parts of the world. He tells him that he got into investment trouble when he was just 19; if he gets convicted on anything at all now, as a “repeat offender”, he gets 25 years to life. This is why he isn’t being more helpful to George. George is frustrated with his father’s attitude about business and calls him an ethical mutant.
While packing to leave for a roadtrip, Lisa asks Mattie if he is monogamous. He says “essentially”. She is incredulous at the response, and tells him that she is moving out. He talks her into still seeing him, so they can work it out, and she agrees. He says they both need to be monogamous, but live apart.
Lisa goes to watch her teammates play ball; afterwards, she is upset, and goes to George’s apartment, and stands out front and phones him. He is working and hears her voice outside the open window, and talks to her on the phone while she has no idea he has seen her. She wants to come and hang out, and says she’ll be there soon. After she gets there, George gets a phone call from Annie that she just had the baby, so they both go to see her in the hospital. She had a beautiful 10 pound baby boy, and then the baby’s father, Al, arrives. Al asks George to tape this, and tells Annie that he never talked about marriage because he didn’t have much to offer and was kind of a failure. But, he realized that she needed someone who loved her just the way she was, and appreciated her worrying as genuine concern and love for others, and wants to be that guy. He proposes they get married, and she accepts. They ask George if he caught it all on the video, but he got so excited in the moment, that he didn’t start the tape. Lisa and George remind Al what he said and they basically reenact the proposal so they can stage a re-taping, and they are moved and touched by the remark, and we can see both George and Lisa think about what was said.
Leaving the hospital, it is an emotional moment between George and Lisa, and as they start to talk, her bus comes and she gets on. It pulls away and she sees George motioning in anger. She gets off the bus and goes to him, to ask what is wrong. She tells him she isn’t living with Mattie anymore, but that he is having a birthday party for her tomorrow. Finally being assertive, George asks if he can come to the party, and she says of course.
Before the party, George goes to see his father. He has a huge team of lawyers there, and they step outside. George tells him he decided what he is going to do: if he has any chance with Lisa, then he is going to cooperate and try for exoneration. If it is hopeless, he will take the hit and go to jail for 3 years, to protect his dad.
At the party, Mattie pulls Lisa aside and gives her a birthday present: it is a lavish diamond watch. She is surprised, and asks him where she would wear something like that? He tells her that he’ll take her places she can wear it. While being a generous beautiful gift, Lisa is uncomfortable that it is too much, and “not her”. She wears it at the party. George asks to talk to her, and they go outside. He also gives her a gift: she opens it and it is a can of Play-Doh. He tells the story of Play-Doh, that it was initially a cleaner for soot removal during the time people used coal, but when things changed to gas and electricity, it was about to be obsolete. The inventor’s sister suggested he color it and sell it as a toy, since her kids prefer its softness to that of modeling clay. He told her that he felt this story was meant for her at this time in her life. She loved that thoughtful gesture, and kept the Play-Doh. As the party ended, George told her he needed to talk to her, and that he’d wait outside at the bus stop, if she could come. As the party ended, she told Mattie that she needed to go hang out with George. Trying to be nice, he says ok, and then realizes that they are over, and asks her what he did wrong? She tells him he didn’t do anything wrong, and kisses him good-bye.
George is pacing, waiting, and his father looks over the balcony of his apartment and sees his son below. He watches as Lisa comes to him, and they sit on the bench together. George kisses her, a long kiss, and they sit and talk. She tells him she first thought he was just this silly guy, but he is anything BUT silly. He tells her he knows what she is trying to say: that she loves him, too. Lisa reaches over and holds his hand.
The bus pulls up, stops, and as it leaves, no one is left sitting on the bench.
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