How can we make our gift-giving more meaningful, especially after years of repeated gifting? Play with context. Some relationships, as they mature, settle into familiar rhythms. This is part of their beauty and comfort, for sure.

Yet, if we strive to make our connections an ongoing discovery - of ourselves and our loved ones - we have a unique opportunity with gift-giving to expand. In particular, I am thinking of a switch in tone. If we have, for years, given a sentimental or earnestly meaningful item - we can try for whimsy! If, inversely, we have always been playful and silly with one, we could switch it up and go for heart-felt.

For example, your brother-in-law is a serious fellow. He’s an accountant and his idea of a good time is an evening at the opera. He loves music, but in a way that’s always been a bit intimidating for you. You’ve done the season tickets for him and your sister. You’ve done the planners and organizers. Yawn. Ok, time to mix it up!

This year, you could try something related, but with a whole different spirit. A guitar-shaped ring holder could be just the thing. It speaks to his love of music - but stretches you both out of the familiar art of gift-giving comfort zone.

Maybe you get to see a humor and delight about him that you’d never noticed before. Maybe he feels a relief for you allowing him the freedom to embrace his inner rock-star.

Likewise, if you always give your sister a goofy, gag-style gift… why not try a more significant piece? A hand-crafted fruit bowl could actually be that message of, “I see you are grown-up now.” that your sister has been longing for from you.

Consider that the way we gift is a chance to expand how we interact with one another. Have fun, and watch a new spark between you arise!