This is the story about a wealthy businessman who falls in love with the janitor lady who works for his company. Tyler Perry plays the lead character of Wesley Deeds. He is a very successful businessman. Mostly his mother Wilimena (played by Phylicia Rashad) has planned his entire life out for him. He is about to get married to a woman named Natalie (played by Gabrielle Union) who is going to take over running his schedule of the same daily routine. Lindsey Wakefield (played by Thandie Newton) works as a janitor for his company. She is broke and about to be thrown out of her apartment.
Wesley has to drive his brother Walter (played by Brian J. White) to work because he had too many arrests for drunk driving which caused him to lose his license. Walter complains someone needs to call the judge and fix the problem for him, saying if their father were still alive, he would do it. Wesley says he can take it up with their mother when they have lunch with her that day.
When Lindsey gets to the company, she cuts off Wesley to take the available open space. She parks in the special space reserved for Wesley Deeds, just so she can run in quickly, get her check, and go get the balance of the money she needs to pay the rent to avoid eviction that day. She leaves her little girl named Ariel (played by Jordenn Thompson) in the van. Walter calls after her, yelling she cannot park there. She tells him off and enters the building without moving the van. Walter calls to get the van towed. Before they take the van, Wesley sees the young girl in the back seat. They stay in the parking lot until her mother comes back.
Lindsey gets her check but it is way short. The IRS has garnished her wages. She comes back to the van to see it is being towed. She fights with Walter again. Walter tells her she is a bad mother for leaving a child in the van. Wesley tells the tow truck driver to put the van down and let her take it. Lindsey rushes Ariel to her school. They arrive very late. The principal chastises her and says if she continues to bring the child to school late, she will call child protection services. When Lindsey gets back to her apartment, her stuff is already in the street and people are picking through it. She finds out the money, she was saving to pay the rent, has been stolen from her things. She picks up some of her things.
Wesley learns they are losing a client because of a deal Walter screwed up, which represents 75% of the company's business. Wesley's adviser, a guy named John (played by Eddie Cibrian) tells him the rival company, which stole their best client will not be able to service the deal. This actually makes them vulnerable for take-over.
Wesley with his fiancée, Natalie, and Walter with his wife have lunch with their mother Wilimena. Wilimena attacks Walter for drinking at lunch, saying she did not even want to see him, but Wesley forced her. Now she is even more disappointed since Walter caused the company to lose the majority of its business. Walter screams at her, saying she only cares about money, then storms off. Wesley stays composed throughout all of the fight.
Lindsey picks up Ariel late from school after she gets off work, then goes back to work to do a second shift. She hides Ariel in the janitor's closet at work. She is caught making a personal call on the company phone by Wesley who is working late. He tells her, she could be fired for doing such a thing. She tells him to please not tell the big white boss, Mr. Deeds, who owns the place. Wesley tells her she should never leave her child alone in her van like she did earlier. He says when he was a child, he was left alone and almost drowned in the ocean not knowing the surf was so strong, but his life was saved by his younger brother Walter. Wesley goes back to his office. When her shift is done, Lindsey takes Ariel out to the van. They are out of gas. Wesley sees them as he leaves. He sees Ariel is with her. Lindsey lies and says a friend is coming to help. Wesley tells her his secretary was mugged in the parking lot so it is not safe for her to be alone, so he will wait for her friend to show up. He introduces himself as Wesley Deeds, the “big white boss” which is funny because he is African American. She thinks she is being fired, but instead Wesley offers to take them for pizza, realizing there is nobody coming to help her.
They have a good time together. When he leaves a big tip, she swipes some of it when he is not looking to get money for gas. Wesley leaves them at the van, then goes home. Wesley gets home first before Natalie. Natalie comes home drunk. She makes the moves on him but he is too uptight to have sex with her in such a condition, which makes her angry.
The next day Lindsey tries to find a place in the homeless shelter. When school is out she brings Ariel back with her to work, and hides her in the janitor's closet. Wesley while working late once again, spills coffee on his desk. When he goes to get some paper towels, he finds Ariel in the closet. He takes her back to his office. When Lindsey sees her daughter is missing she panics, until she finds her with Wesley. They stay one night at the shelter but they are attacked by another homeless person trying to rob them. Ariel's school finds out they are homeless, so the child protective services takes her away until Lindsey can prove she has an apartment.
Wesley's friendship with Lindsey helps him lighten up. He has great makeup sex with Natalie because of this, which surprises her. He dresses more casually and seems to be able to finally let himself go a little. Walter notices Wesley taking Lindsey out for lunch. Wesley allows her to stay in a company apartment for free. She gets Ariel back. Wesley told her he used to like motorcycles before he got so busy working, so Lindsey convinces a dealer to lend them one for a test drive so they can go for a ride. They have fun riding through the countryside north of San Francisco and stop by a small beautiful lake where they kiss. Wesley tells her there is a problem; he is already engaged. This surprise hurts Lindsey. However; she maintains composure, congratulates him, and then right after they get back, she runs off as quickly as possible to get her daughter from school.
The competing company agrees to the acquisition deal. Wesley, Natalie, Walter, Wilimena, and all the rest of the company staff are going to a have a celebration. Walter drags Lindsey in to introduce her to both Natalie and Wilimena as Wesley's newest friend, a janitor. Natalie wonders is Wesley is having an affair with her. Wilimena says Wesley is always doing kind projects, which hurts Lindsey. Walter screams at his mother, then storms out taking car keys. Wesley knows he is not supposed to drive, especially in such a condition. Wesley tries to stop him and they end of physically fighting.
Later, Wesley tries to make it up with Lindsey but she is not sure, if his feelings are sincere or if she is just some kind of project. When Wesley returns home Natalie ask him if he slept with her. He says no. However; they both realize their marriage would be a mistake under these circumstances, so they call off the wedding. Wesley wants to take some time off to visit Africa, which has always been his dream, so he puts John in charge of the company. Wilimena is mad, Walter is mad, but it is time for Wesley to do something he really likes for himself. He invites Lindsey to go with him and bring Ariel. Lindsey refuses because she is still not certain of his intentions. He gives her tickets just in case she changes her mind. At the airport, they are not there. He leaves on the plane by himself. He is very pleasantly surprised when both Lindsey and Ariel are already on the plane, having boarded before he got there. Ariel smiles when they kiss.
Best part of story, including ending:
I like that Lindsey, the poor janitor, has what the rich man Wesley needs the most, which is teaching him how to have a good time.
Best scene in story:
I like the scene when they first kiss by the lake during the motorcycle tour because it is tender.
Opinion about the main character:
I like when Wesley finally gives himself a chance to take some time off, and to live a little because there is more to life than working all the time.