Hitch

This movie features Will Smith. This movie is an older, more original Will Smith movie. 

Throughout the movie, Will who plays Alex has a service that is supposed to help you get more comfortable with talking to women, helps you with your game, etc. The main guy Alex is helping out with is named Albert. He is a shy, awkward, and all-around lost fella when it comes to women, and honestly his life. Albert is madly in love with Allegra, who works for. Alex gives Albert pointers to help Albert get her. Albert struggles to actually follow Alex’s advice and finds himself in a twist.