Hitch (2005)

Described as New York City's finest date doctor, suave matchmaker Alex "Hitch" Hitchens can guarantee that any man can get the girl of his dreams if he overcomes his fears and follows his infallible advice. And then, timid accountant Albert Brennaman enters the picture. As the hopeless man enlists the doctor's help to catch the attention of beautiful heiress Allegra Cole, something unexpected happens: Hitch discovers inquisitive gossip columnist Sara Melas, his dream match. Now, the self-assured charmer must put his expertise to good use to make it happen. However, can the silver-tongued romance expert survive love's delicate complications?