Maybe this has happened to you. One fine day when you’re walking down the street, minding your own business, you feel something brush by you. So you check your pockets, and pull out a twenty dollar bill.

Maybe this hasn’t happened to you. In fact, usually when someone picks your pocket, they’re trying to take money. The world is full of pickpockets, pilferers, purse-snatchers and petty thieves. But there’s a way to give someone a more pleasant surprise for a change.

I learned the art from my grandfather, one of the most generous people in my life. Since I was little, he would practice the art of giving me a hug, only to slip a dollar in my shirt pocket. The trick, of course, was not in going unnoticed, but in the audacity of trying. I usually caught him in the act. The trick was in giving it before I could refuse.

Sometimes people have a hard time accepting a gift. Maybe they’re too proud, too ashamed of their need, or don’t want to feel like a burden on others. Try to hand them some money and they may refuse to take it outright. It is easy to decline a gift before it leaves the giver’s hand.

But if they don’t notice you’ve given it to them until they already have it, rejecting the gift is hard to do. They now have to take it and put it back in your hands, which could appear offensive to giver.

Then there’s the humor aspect, a hallmark of my grandfather’s hijinks. There’s a bit of the prankster in him, and so the sneaky giving is done a bit tongue-in-cheek. Sometimes a person doesn’t want to feel pitied, but giving with a wink of the eye distracts from those anxieties, as if to say,

“I give you this because I like you, and I thought you’d enjoy this. Also, wasn’t it funny?”

The subtle nature of this act of giving also keeps it secret from others. For various reasons, the recipient may feel uneasy about everyone seeing them receive a gift. Why them? What problems to they have? Why can’t they take care of themselves? By slight-of-hand, giving in secret can avoid the stigma of receiving gifts in front of other people.

Of course, if the recipient is stubborn enough, they can also return the gift secretly, maybe even make a game out of it to avoid the awkwardness of refusal. This could even keep going, free concert tickets winding up all sorts of places. In this way, a friendship could even be built or maintained because of a generous prank.

The principle behind reverse pickpocketing can apply elsewhere. Think of other ways you can make the act of giving look something else entirely. Or how you can help someone overcome the stress of receiving money or some other gift by making a prank out of it. There is no reason to be showy.

Most of all, what I love about my grandfather’s habit of giving is that it usually comes with a hug. The hug and the dollar were both important. I don’t love my grandfather just because he is willing to shell out some money. I love him because he is a warm and compassionate man. His generosity showed, but it was also felt.

He still manages to get away with it, even though I’m old enough to have children of my own. He’ll tip his hat goodbye, and an hour later I find ten dollars in my rear pocket. How did he do that?

So try it out sometime. Take a ten dollar bill, or maybe even just a single dollar, and try to slip it into a friend’s pocket. If they notice, see how they react. Take note. It may inform your practice of kindness in the future.

That being said, I would not recommend literally trying to reverse pickpocket a stranger in the streets, unless you’re adept at not getting caught. It may be real difficult to explain to the police that you were trying to sneakily put money in a person’s wallet rather than take it out.

Reverse pickpocketing. Give it a shot. Make sure to slip in a kindness card too, while you’re at it.