I've done it before. Not with groceries but with other things.
I wouldn't have done it like old girl though and certainly not at Walmart or CVS. Go big or go home.
I would ask before I picked up something. Men are easy to hustle if you look good.
Wouldn't do it now but asking a man for something is the quickest way to get him to either leave you alone or get it. You got a 50/50 shot. That's why it's funny when people say men don't give money, buy things w/o sex. That shyt is so not true. The tiny glimmer of hope in him mind is enough.
I told the story on here before about getting my parking ticket paid by a random.
The funny part is that he was more interested in my friend than me. I even had random men OFFER to pay for things I was buying in the store.
It's always the 35+ men with a little bread. I look young so they always assume they can out smart me or impress me with a little cash.
God I have stories for days about getting these dudes. Not on that now but catch me in the right mood and I might try you.
Eta: There are different types of men. I would never try to hustle a nice guy. An ass hole though is fair game.