Some Gifts Don’t Want to Be Asked For

Aug 26, 2025

Fundraising has long been preoccupied with the ask. We train for it, script it, rehearse it. Entire fundraising campaigns live or die by whether the ask is bold enough, clear enough, personal enough. But this morning, over something as small as a Wawa coffee roll, I was reminded that not every gift wants to be asked for. And that simple reality might have something to teach those of us who raise money for a living.

The Coffee Roll That Showed Up

You can’t live in Pennsylvania as long as our family has and not become a fan of Wawa. For more than twenty years, I’ve been making regular stops for their coffee and on good days, a coffee roll too. Lately, with teenagers in the house who frequent the new Wawa across Route 30, I’ve gotten into the habit of asking them to grab me a cup when they go. Most of the time, it’s a non-event. They return with my coffee, and I’m grateful.

But sometimes, the ask carries weight. A teenager on a tight budget doesn’t always want to spend a few extra dollars on dad’s coffee and certainly doesn’t want the added obligation of a coffee roll too. Asking changes the equation. It introduces expectation. It shifts the emotional balance.

This morning, my oldest daughter Christina and I left the house early, coffee from home in hand. I was driving her to work before heading on to a breakfast meeting in Lancaster. We stopped at Wawa on the way. She ran inside, and when she came back to the car, she handed me one of those enormous coffee rolls. I hadn’t asked for it.

The Gift That Wanted to Surprise Me

On the drive to Lancaster, coffee roll in hand, I realized what that small gesture was telling me. Some gifts want to arrive unsolicited. Sometimes the gift wants to let the relationship do the heavy lifting.

When we don’t ask for the gift, the giver gets to surprise us. They get to see us, to understand what might bring a moment of delight. They get to give freely, without the weight of obligation or the shadow of expectation.

The unasked-for gift doesn’t carry a ledger. It doesn’t create a sense of debt or the faint aftertaste of a grudge: I only did this because you asked. Instead, it carries the quiet joy of someone acting on their own accord, in their own timing, with their own sense of what might bless another.

What Fundraisers Might Learn

Far too often, we cross our fingers hoping what worked before will work again, or we borrow tactics from the marketplace and hope they’ll translate. What we rarely do is pay attention to the countless other places in our daily lives where gifts are exchanged. My guess is that paying closer attention would require focusing less on what’s being exchanged and more on the relationship itself.

None of this means we stop asking. Fundraising will always require skillful invitations. But maybe we’ve made the ask too central, as though generosity can only be coaxed into existence through carefully managed technique.

What if part of our work was simply to make space for surprise? To create room for givers to act on their own initiative rather than ours? To let generosity sometimes arrive on its own timetable rather than the one set by our campaign calendar?

The coffee roll this morning was a simple gesture. Christina may not have given it much thought, or perhaps she did. But it reminded me that gifts carry their own logic. Some want to be planned, some invited, some stewarded, and some, every once in a while, simply want to show up unsolicited.

Jason Lewis

, Founder, Responsive Fundraising