When a guy be going around and messin around with mad amounts of girls. Basically being a man hoe. Stealing their virginity or popping their "cherries".
When trimming bud and paid by the pound, a cherry picker is one who takes all the biggest buds for themselves, leaving the smaller buds for everyone else.
E. Is a cherry picker of the most blatant kind, not caring who knows, she just forges ahead and claims her pound per day while everyone else gets a half.