Most of my extended family and friends live in far-flung places. We can't visit them all in any given year, and there are too many to send gifts to annually. I'd like to send gifts (usually "Boston boxes" of regional goodies) to people we've stayed with in a given year, or who've helped out my elderly parent during the year. But I don't want this to seem transactional, nor do I want people to feel they have to send a gift in return. How do I tastefully do this?
First off, as the holidays approach, I love your idea of "Boston boxes" and encourage readers to recommend their own favorite local vendors in online comments or e-mails to me. Gift-giving is best when you're as pleased to give your money to a worthy vendor as you are to share their product or service with a loved one. Not always an achievable goal, but one worth aiming for. What have you got, readers? Spill that tea.
But you weren't writing to give advice, you wanted to get some, so here goes: Think about changing your timing, because end-of-year gifts come in two flavors -- Traditional and Transactional -- and you don't like the taste of either. If you don't want the far-flung family and friends, the F.F.F.F.'s, to feel unwillingly roped into a Christmas-gift loop, or worse yet to feel tipped for the year's good service, send their goody boxes during another season.
Keep making the boxes an annual event, if that's convenient and fun, as long as you're thanking your hosts promptly as well. (Of course you are!) But pick a time of year that isn't already overburdened with cultural messages about Gifts And What They Mean. Pick a different holiday that's meaningful to you, or a fun themed season: Back-to-School? March Madness? Christmas in July? You can still shop at the local holiday art fairs and stash your finds away for later.
Mind you, your F.F.F.F. may be taking your gifts in exactly the manner intended, especially if the boxes are preceded or followed by a contextualizing call or e-mail. You may not have a problem at all! But if you do, this will help.