The movie opens with Will Smith's character AKA Alex Hitchins talking about how men just need that little push to get the woman of their dreams and how he helps them do that. All he needs is 3 dates and usually after that 3rd date its love - he pretty much can guarantee that.
We then see a flashback to when Alex was in college. He is definitely not the coolest person on campus (go back to Fresh Prince era with glasses). He meets a girl and they instantly click and we see them kissing and Alex explains to her how he is in love with her and we think she feels the same (maybe not as much as him), but he finds her in a car with another guy making out. Alex is upset and screams that he just wants to know why this has happened" and all she can say is she is sorry.
That basically explains why he wanted to start the secret date Dr. business. The only men he will help are ones that are referred to him. We also see in the beginning a woman named Sara (Eva Mendes) going back to work from a short vacation with big news about a man who cheated on an heiress named Allegra Cole (Amber Valletta). While Sara was on vacation she spotted the cheating man on the same beach she was at and had to come back to work to write the article for her gossip column New York Standard. This pleases her boss and he praises her for her hard work, but questions that she may be working to hard at her job and not at her personal life. She doesn't seem to concerned and blows the subject off.
That evening we see Hitch out at a bar with a pal playing pool. Hitch has to prove to his pal that he can get any girl to come over and talk to them and he seems very confident. At this same time we see Sara at the same bar talking to her friend Julie( Julie Ann Emery) Julie is explaining to Sara about a guy she met at a lingerie store and how he said he was there buying something for his mother and they exchanged phone #'s. Sara doesn't buy it and says that the guy was definitely not there to buy something for his mother, but Casey seems desperate enough to believe the guy.
The next day we see Hitch standing outside of a building watching an overweight man who is very clumsily eating a hot dog. Hitch is amused at how awful this guy seems and introduces himself to the man who's name is Albert. (Kevin James) Albert explains that he needs Hitch's help in getting to know a women who he is head over heels for. It turned out to be Allegra Cole (the heiress whose boyfriend was caught cheating on her). Albert also works for Allegra as one of her financial advisers. Hitch is highly amused that Albert would even go as far as to liking a women like Allegra, but he agrees because he can see that Albert is sincere and does seem to have true feelings for Allegra.
Then begins the training that Albert has to do to get close to Allegra. Hitch tells him the first thing he should try to do is something over the top impressive to Allegra. We see Albert in a business meeting with his fellow colleagues and Allegra. Allegra has a suggestion for how she would like to spend some of her fortune and explains that she has a friend named Maggie that is wanted to start a fashion line and she would like 1/2 million dollars to invest in this. The lead adviser says that he thinks it can be worked out, but he wants a month to make arrangements. This disappoints Allegra because it is something she really wants now. Albert speaks up and begins to take sides with Allegra, saying that this is her money, she should do what she wants with it and since she is an adult she shouldn't have to ask what she should to with it. The lead adviser is shocked by Albert's reaction, but in the end Albert said he would just quit this job.
He goes back in his office where Hitch is. Albert is so uptight about what happened and takes out his asthma medicine. Hitch and Albert have a scuffle so Albert can calm down. During the scuffle Allegra knocks on the door and tells Albert she is shocked about what just happened, but wants to get with him this week to go over some things about the plan for her friend's fashion line. He nervously agrees while Hitch is never seen behind the door.
That night Hitch is back at the bar we saw him before, as is Sara. We see a man coming on strong to her and she politely says she isn't interested but he won't go away. Hitch sees what is going on and comes over and acts like he is with Sara. He asks her how her meeting was and she plays along and the man takes the notion that they are really together. Hitch and Sara have a flirty conversation about dating and they introduce themselves, but Hitch leaves the conversation short, leaving her extremely interested and impressed.
The next day we see Sara get a package at her work place. It ends up being walkie talkies and Hitch is on the other line he asks her to go out on jet skis with him. She turns him down once, but he is persistent and she agrees to and then she receives another package from him with a wet suit inside. The date ends up horrific. Will kicks her off her jet ski, he digs up some information about her family history which he thinks she will be impressed with, but it also turns out to be bad, but she isn't too upset in the end and we think they will see each other again.
We also see Hitch help Albert plan a day with Allegra. This time they are going to a fashion event to meet her friend Maggie. Hitch helps him learn how to dance properly, but he doesn't get it. The date isn't perfect by no means. Albert meets Maggie, who ends up being a man, so he is a bit tongue tied as to what to say. He also dances awful and reporters capture it with their cameras, but Allegra seems to be having a good time with him.
The twist now comes into play. Hitch meets a prospective client named Vance. (Jeffery Donovan) Vance says he just wants to get in bed with someone he met a lingerie store (Sara's friend Casey) and thinks Hitch will be able to help him to that fast. Hitch doesn't like this guy at all and tries to leave, but Vance thinks money can change his mind. Hitch explains that this job isn't to help men like him and leaves.
We then see Sara and her boss discussing gossip that got out about Allegra being at an event with an unknown man (Albert). He is upset that Sara didn't get the scoop and wants to know what is going on. Sara finds out that Hitch is the one who got the tickets to this event for Allegra and Albert. She asks him how he knows them. He says he doesn't know them and tries to deny it.
Later, Sara asks him to dinner and her boss ends up being there and they both try to get more info on Allegra and Albert. While they are eating Hitch begins to have trouble swallowing and begins to have an allergic reaction to the food. He swells up like a balloon and gets drugged up on Benedryl. Sara again tries to get more info out of him, but he doesn't really budge, but does tell him that the two are going to the Knicks game tomorrow night. Sara ends up going to the game to get photos of them for her column.
The next day we see Casey upset about her date last night. She slept with the guy at the lingerie store, but he had left her in a hurry. She said she would like to kick the date Dr. that so called helped the man she went out with. Sara finds the jerk that Casey went out with to see who this date Dr. is. All he can tell her is where she could find him he doesn't know his name. So, she sets this date Dr. up to meet a guy friend of hers on a fake meeting. She finds out that the date Dr. is Hitch and is upset but runs off instead of asking him what is going on.
She is so upset that she ends up writing a gossip article on him exploiting the situation without getting the right facts. She also includes Albert and Allegra in this so Allegra thinks that everything was an act. Albert is crushed and Hitch is ruined.
Hitch is upset that Sara didn't get the facts before writing the article. She ends up learning the truth and apologizes to Hitch, but he is too upset to accept this and blows her off. Later, we see Hitch preparing to move out of his apartment and Albert comes in to ask Hitch if he can fix this situation. Hitch is bitter about everything and thinks love is over rated. Albert tells him that Hitch was a liar for what he did to all the men he helped. He shouldn't help men out with love if he doesn't believe in it.
Albert leaves upset and Hitch begins to think about everything. He decides to help Albert and runs to meet Allegra to tell her that Albert wasn't acting about how he feels for her. that all the dorky things he did on their dates was really him. Allegra believes him and she takes Albert back.
Hitch then goes to Sara to tell her his feelings, but he has a difficult time. Now, he is the one needing a date Dr. to get his words right. Sara isn't buying it and tries to tell him to leave, but he doesn't. He ends up telling her how he feels about her, but Sara opens the door and there is another man there. Sara says its to late and starts to leave with the man. Hitch goes after them and he jumps on their car and she finally stops. The man ends up being her brother in law and she takes Hitch back. They have a sweet reunion and in the end we see Albert and Allegra at their wedding. Everyone's happy :)
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