To check out a person of the opposite sex whose league you are out of, in the attempt to make them feel good about themselves. Helping the community one ugly girl at a time.
That busted chick was checking me out, I gave her the ill Jack Charity.
A word made famous by a man named Jack Conery, when he would give a really ugly girl the eye to raise her self esteem and make her feel good for the rest of the day.
Yo I just gave that girl the crazy jack charity, did you see how busted she was?
Legend has it, a man named Jack Conery would give very ugly girls a sexual look to increase their confidence and self-esteem
Yo i just gave her the crazy Jack Charity, did you see how busted she was?