How do you help someone who is lacking confidence?

Confidence comes with experience ,you can't buy it ,there are no short cuts
A coach can hype you up .a self improvement tape may tell you area's to work on ,,but confidence comes from getting good at something

PS ,,tell him to learn to play guitar and join a band
chicks like musicians ..all of my wives chased me
I was shy too ..not on stage ,but face to face
I had to ask my wife to marry me by singing her a song

Hire an escort for him. Just don't let him find out you paid her. She should tell him it's just a one-time-hookup.

Use reverse psychology. Tell him he's right and has to leave all the women to you.

That’s the least of his problems.

Maybe he is gay