The Life Coach

Example used: Sting
Other options include singers of famous songs with girls names in them.

Opening scene: Bar, attractive woman with martini, empty seat to her side.
Loser enters: (imagine Jonah Hill type.) loser approaches bar, orders a drink and asks her name in what he imagines is suave but is actually a poor attempt.
She replies, "Carol"
"Are you sure its not "Roxanne"" Which he beings to sing loudly and obnoxiously.
She runs away in disgust.
Camera pans following Loser walking to the other side of the bar see him sit down
Loser: "I don't get it I did exactly what you told me and it didn't work at all"
Switch camera now focused on Sting on the other side of the booth. Pause for a second.
Sting: I don't understand, it always works for me.
Sting goes up to incredibly attractive girl. She is not looking at him
Sting: Whats your name?
She turns around and is immediately enamored with Sting. Says, "Megan".
Sting: "Are you sure it's not Roxanne" tears shirt off begins to sing, guitar is lowered lights change background musicians come out.
She swoons. He puts down the guitar, she jumps into his arms and he carries her away.

Possible follow-up scene. Short scene of Loser reattempting this time with taking off his shirt.