playing confidence man

Playing Confidence man is when a guy willing dates or acts interested in a woman to raise her self esteem

Linda: "Wow I didn't know Rob was into Michelle"

John: "He's not, he's just playing confidence man"

Confident man

OOOOHHH!!! MYGOD!!! THISFUCKINGGUY!!!

Hym "The picture... Is 2 women staring at his fat cock... One overtly and the other is kind of side-eyeing it... What about that has anything to do with being a confident man? 'You see how confident I am in women's endless desire for fat cocks?' We're in euphemism land! We're in pretend euphemism land! Confidence? Jesus Christ!"