Improving the odds for successful gift-giving

How a gift feels matters as much as how it’s structured. Three studies on giving well, including gifts of money.

By Dave Jones, JD, LLM, CFP®, Director of Estate Strategy

 

For something meant to bring joy and connection, gift-giving can create a surprising amount of pressure, especially around the holidays. As the occasion approaches without a thoughtful gift in hand, it can follow us to work and keep us up at night. Even though we know our loved ones well, finding something that will truly make them happy can feel impossible.

Part of the problem is the gap between what we think our loved ones want and what they actually want. We buy gifts they wouldn’t buy for themselves, and plenty of those end up returned or re-gifted.In estate planning, I spend a lot of my time on the mechanics of giving, like exclusions and exemptions. What families tend to remember, though, is how a gift felt.

This article looks at three research findings that can improve the odds of a successful gift, one that brings more happiness to both giver and receiver.

Should gifts reflect the recipient or the giver?

We all want gifts that reflect our interests and desires. As a kid, I didn’t want a new lawnmower (something my Dad would have wanted). I wanted a pair of Air Jordans. Thank you, Mom! But we don’t always know what the receiver truly wants, so we end up guessing. One study suggests focusing on yourself instead.

That’s right. If you don’t know what the receiver wants, consider giving something important to you. Across several studies, Lara B. Aknin and Lauren J. Human found that despite givers’ overwhelming preference for a recipient-focused gift, “giving a gift that reflects the giver’s true self actually led both givers and receivers to feel closer to one another.”

When the goal is connection, a gift that shares something of you can do more than one based on a guess about the other person’s tastes. Think of a favorite book, a family heirloom, or a bottle of wine (intended to be shared).

My grandfather was an expert at this. Several years before he passed, he started a tradition of bringing some of his collectibles to our family’s holiday gatherings. Everyone in the family (and there were lots of us) took turns choosing one as a gift from him. There were instruments (violins, ukuleles, flutes), weapons (massive Bowie knives and machetes), paperweights, coins, and a myriad of other pieces. It was so much fun to see what he had collected, and even better to spend one-on-one time with him afterward as he shared his knowledge about the item we chose.

Should the giver ask what the receiver wants?

Asking what a family member or loved one wants can feel tacky or read as lazy or inattentive. But asking tends to go over better than we’d expect.

In “Give Them What They Want,” Francesca Gino and Francis Flynn conducted five studies examining how people responded to solicited versus unsolicited gifts, using wedding registries, birthday lists, and Amazon.com wish lists. In each case, recipients appreciated gifts they explicitly requested more than gifts they did not. The interesting part was the mismatch in expectations: gift givers assumed an unsolicited gift signaled more thoughtfulness and consideration than recipients actually perceived.

Also, givers were more receptive when recipients named one specific gift than when they were offered a list. The catch is timing. A request the day before an occasion will feel insensitive, and a gift that matches the request to the letter leaves little room for surprise. Asking early and casually, or noting what comes up through the year, tends to land better. A requested gift paired with a small, unexpected one is another option.

If the goal is the recipient’s happiness, asking what they want is often a better strategy than guessing.

Should gift-givers wait until special occasions?

Not only then, and the reason is worth a closer look. Julian Givi and Jeff Galak studied what recipients expect to feel when a gift arrives on an ordinary day versus an occasion.

In their words:

“When the gift was given on a miscellaneous day, recipients anticipated that they would be just as happy receiving a single rose as they would receiving an entire bouquet, but when the gift was given on Valentine’s Day, recipients anticipated that they would be far less happy receiving a single rose versus a bouquet.”

Because an unexpected gift carries fewer expectations, it may not need to be perfect to land well. The authors also note that gifts on ordinary days are relatively uncommon, which suggests givers may be missing easy opportunities to bring joy.

Occasion gifts still matter, though, because they signal care and meet expectations. Ordinary-day gifts work best alongside the special ones. You can even combine strategies. Take a loved one to their favorite restaurant on an ordinary day, and ask for their wish list!

What this means for financial gifts

One of the Gino and Flynn studies is especially relevant here. Recipients appreciated a gift of money more than any item they had requested, even though givers assumed cash would be the least welcome option. Many of us hesitate to give money because it feels impersonal. The recipients in that study didn’t see it that way.

Each of the three findings has a parallel. A note about why you’re giving, or what the money represents to you, makes a financial gift reflect the giver. Asking what a child is saving for, or what’s weighing on them financially, is the financial version of a wish list. And a gift doesn’t need an occasion. Help with a car repair in March, with no holiday attached, may mean more than you’d expect.

Estate planning can feel transactional because so much of it is technical. My grandfather handed down his collectibles while he was still here to explain what they meant, and that is the part I remember. Financial gifts can work the same way. Share more of yourself, be curious about what they want, and make giving an experience throughout the year.

The federal gift and estate tax rules, along with a few trade-offs worth weighing, are summarized in “How the 2026 rules work.” If you are considering gifts to family this year, we are happy to talk it through with you and your tax advisor before you give.

 

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The tax rates and rules described in this article reflect Federal law in effect as of the date of publication and are subject to change. This material is provided for educational purposes only. Neither Bailard nor any of its employees can provide tax or legal advice. Please consult your tax advisor regarding your particular situation.