Lisa Jorgenson (Reese Witherspoon) was a talented softball player. She was very popular among her teammates.One day, during her training, she received a phone call from a young executive, George Madison (Paul Rudd). A girl friend of Lisa gave her number to George. George called out of politeness just in case Lisa was waiting for his call. However, Lisa politely answered his call and told George that she wasn't expecting his call as she didn't know about him having her number. Anyway, Lisa at that time was dating a handsome, playboy pitcher for the Washington National baseball team, Matty Reynolds (Owen Wilson).
However, life took a sharp turn for both of them. George suddenly found himself under federal investigation for corporate malfeasance at a company run by his father Charles Madison (Jack Nicholson). Feeling confused, George went to find his girldfriend but instead of comforting him, she wanted to break up with him. His sudden dismay caused him to be in a tensed up mood. One night, his pregnant personal assistant, Annie (Kathryn Hahn) called him and advised him to go date a girl to redirect his attention. He thought of Lisa. He called her and he got a date with her. On the day of the date, Lisa received a bad news as well. She was not selected for the new team. As she was over 30, she was dropped off from the latest team line up. During the meal, both who were irritated by their recent situation got into a heated conversation with Lisa requesting to have a quiet meal with George. Both didn't talk throughout the whole meal.
George who lost his job and was not able to contact any of his colleagues except his father found himself in love with Lisa. George found Lisa amazing. At the same time, the playboy Matty also found himself falling in love with Lisa. Matty invited Lisa to live with him at his uptown condominium in Washington D.C. Not knowing what to do next in her life, Lisa accepted the offer and moved in with Matty. Matty made millions of dollars a year and was very fun to be with but he was also immature and was never concerned about Lisa's feelings. Coincidentally, George's father, Charles also stayed in the same building with Matty.
With Annie's help, George also found a new apartment for himself. Annie who was so loyal to him tried to give him inside news regarding his charges. George urged her not to tell him because that would cost her job. Moreover, she was expecting a baby and she needed the job. After much argument and reasoning, Annie decided to keep the news to herself.
One day, George went to visit his father. At the elevator, he bumped into Lisa. Lisa invited him over to her place. While George was there, Matty came home. Matty was furious to find another guy in his house. He got mad. Lisa and Matty got into a heated up conversation, ending with Lisa packing up her things and left. George who witnessed the event chase after Lisa and took the opportunity to get close to Lisa. He invited her over to his place and they had a long talk. Lisa told George that she was unsure if she had got what it takes to lead everybody's regular lives. She was unsure abour marriage and babies. George told Lisa that he was under federal investigation and he might go to jail. That night, they understood each other more.
After much persuasion from Matty, Lisa got back to his place. However, things didn't last long with them. Matty tried to be a better man to Lisa but Lisa found out that Matty still had casual affairs with other women. She decided to move out even though Matty promised her that he would see lesser women. Feeling offended and confused, she went to find George. Whil at George's place, George received a phone call from Annie saying that she just delivered her baby. Both George and Lisa went to the hospital to visit her. While in the hospital, Annie's Boyfriend, Al (Lenny Venito), proposed to her in front of George and Lisa. That night, both George and Lisa left the hospital smiling. She began to reconsider her reluctance in marriage and babies. Lisa told George that Matty would be organizing a birthday party for her. Just before Lisa boarded the bus home, George asked if he could attend her birthday party. Lisa said yes. That night, when George reached home, he called his father. He told him that he was ready to speak to him.
On the day of the part, George went to visit his father first. He asked his father if it was him who committed the illegal act. His father admitted. He then told his father his decision was in the hand of Lisa. If she agreed to be with him, he will not go to the jail. If she rejected his advances, he wil go to the jail for his father.
At the party, Matty gave Lisa a present and rushed her to unwrap the present. It was an expensive watch. Lisa was not very pleasant that Matty had to rush her to open the present. George also came to the party with a present. George pulled Lisa aside and gave the present to her. He gave her time to unwrap her present. It was a playdoh. She was surprised to see the playdoh. He told her that the present was not complete without his explanation. He told her the story behind playdoh and added that everyone were just one small adjustment from making their life work.
After that, George hinted to Lisa that he would be waiting for her at the bus stop downstairs. Lisa thought a while, spoke to Matty and went downstairs to find George. Charles looked from above and saw George waiting at the bus stop. He then saw Lisa walking towards George. Lisa chose George and Charles smiled.
Movie Review - How Do You Know
However, life took a sharp turn for both of them. George suddenly found himself under federal investigation for corporate malfeasance at a company run by his father Charles Madison (Jack Nicholson). Feeling confused, George went to find his girldfriend but instead of comforting him, she wanted to break up with him. His sudden dismay caused him to be in a tensed up mood. One night, his pregnant personal assistant, Annie (Kathryn Hahn) called him and advised him to go date a girl to redirect his attention. He thought of Lisa. He called her and he got a date with her. On the day of the date, Lisa received a bad news as well. She was not selected for the new team. As she was over 30, she was dropped off from the latest team line up. During the meal, both who were irritated by their recent situation got into a heated conversation with Lisa requesting to have a quiet meal with George. Both didn't talk throughout the whole meal.
George who lost his job and was not able to contact any of his colleagues except his father found himself in love with Lisa. George found Lisa amazing. At the same time, the playboy Matty also found himself falling in love with Lisa. Matty invited Lisa to live with him at his uptown condominium in Washington D.C. Not knowing what to do next in her life, Lisa accepted the offer and moved in with Matty. Matty made millions of dollars a year and was very fun to be with but he was also immature and was never concerned about Lisa's feelings. Coincidentally, George's father, Charles also stayed in the same building with Matty.
With Annie's help, George also found a new apartment for himself. Annie who was so loyal to him tried to give him inside news regarding his charges. George urged her not to tell him because that would cost her job. Moreover, she was expecting a baby and she needed the job. After much argument and reasoning, Annie decided to keep the news to herself.
One day, George went to visit his father. At the elevator, he bumped into Lisa. Lisa invited him over to her place. While George was there, Matty came home. Matty was furious to find another guy in his house. He got mad. Lisa and Matty got into a heated up conversation, ending with Lisa packing up her things and left. George who witnessed the event chase after Lisa and took the opportunity to get close to Lisa. He invited her over to his place and they had a long talk. Lisa told George that she was unsure if she had got what it takes to lead everybody's regular lives. She was unsure abour marriage and babies. George told Lisa that he was under federal investigation and he might go to jail. That night, they understood each other more.
After much persuasion from Matty, Lisa got back to his place. However, things didn't last long with them. Matty tried to be a better man to Lisa but Lisa found out that Matty still had casual affairs with other women. She decided to move out even though Matty promised her that he would see lesser women. Feeling offended and confused, she went to find George. Whil at George's place, George received a phone call from Annie saying that she just delivered her baby. Both George and Lisa went to the hospital to visit her. While in the hospital, Annie's Boyfriend, Al (Lenny Venito), proposed to her in front of George and Lisa. That night, both George and Lisa left the hospital smiling. She began to reconsider her reluctance in marriage and babies. Lisa told George that Matty would be organizing a birthday party for her. Just before Lisa boarded the bus home, George asked if he could attend her birthday party. Lisa said yes. That night, when George reached home, he called his father. He told him that he was ready to speak to him.
On the day of the part, George went to visit his father first. He asked his father if it was him who committed the illegal act. His father admitted. He then told his father his decision was in the hand of Lisa. If she agreed to be with him, he will not go to the jail. If she rejected his advances, he wil go to the jail for his father.
At the party, Matty gave Lisa a present and rushed her to unwrap the present. It was an expensive watch. Lisa was not very pleasant that Matty had to rush her to open the present. George also came to the party with a present. George pulled Lisa aside and gave the present to her. He gave her time to unwrap her present. It was a playdoh. She was surprised to see the playdoh. He told her that the present was not complete without his explanation. He told her the story behind playdoh and added that everyone were just one small adjustment from making their life work.
After that, George hinted to Lisa that he would be waiting for her at the bus stop downstairs. Lisa thought a while, spoke to Matty and went downstairs to find George. Charles looked from above and saw George waiting at the bus stop. He then saw Lisa walking towards George. Lisa chose George and Charles smiled.
Movie Review - How Do You Know
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