High school movie, nerd pines for the popular girl, old mentor helps him

"Genre: Drama / Comedy (Coming-of-age) Release year: Definitely not new (older movie, exact year unknown)

Plot Details:

  • The Protagonist: A regular high school guy who is insecure, clumsy, and completely “invisible” to girls.

  • The Crush: He is in love with a very beautiful popular girl at his school. She comes from a wealthy family because her mother is a highly successful model. A key detail about the girl is that she is really into cars.

  • The Mentor: The protagonist tries to talk to her but fails miserably because he is too awkward. He turns to an older man for help (I can’t remember how they are related/connected). This man turns out to be a charismatic ladykiller with a lot of experience with women. At first, the man refuses to help the boy, but he eventually agrees to mentor him.

  • The Plot Twist: Thanks to the advice, the boy successfully gets the girl interested in him. However, towards the end of the movie, the boy finds out a major secret: his mentor used to be in a relationship with the girl’s supermodel mother in the past.

I don’t remember what happens after that. Does anyone know the title of this movie?

And also I clearly remember one specific, rather funny scene from the movie. After the girl kisses the boy on the cheek, he rushes to tell his mentor about it. He is so incredibly happy that he starts shouting with joy: “She kissed me!” An elderly man loses his patience, slaps the boy in the face and tells him to pull himself together."