Listen closely! The single best trick to giving the perfect gift

Listen closely! The single best trick to giving the perfect gift

The annual holiday shopping frenzyis in full swing. People are hitting the malls, big box stores, and Amazon, trying to get the best deal on “stuff,” much of which will be used briefly (or not at all) and then forgotten.

If you follow me online, you know that I’m a huge fan of experience gifts rather than “stuff” gifts. So I put together a list of 88 experience gift ideas for this holiday season.

But reading a list is the easy part. What’s harder is picking just the right thing for your recipient. 

And sometimes just the right thing actually is a thing.

I’ll let you in on a secret

I consider myself a pretty excellent gift giver. I’ve been told I always find just the right gift, and I try to live up to that reputation every birthday and holiday season.

Here’s my secret: It’s not about searching for the gift, it’s about listening to my friends and family all year long and taking note of their preferences, experiences, challenges, wishes, aspirations, and happy memories.

Here are some phrases I listen for:

  • “I wish I had more time to…”
  • “That reminds me of that time my friends and I…”
  • “That was the best trip I ever took because…”
  • “Our whole family loves to…”
  • “That year was so great because…” 
  • “If only I could afford…”
  • “This one time my brother and I…”
  • “The best gift I got as a kid was…”
  • “Remember that time we…?”
  • “This summer we’re planning to…”   
  • “I used to love when my dad and I would…”
  • “When I have a day to myself, I like to…”
  • “I can never find…”
  • “I’ve always wanted to try…”

When you put up your radar for these types of statements, gift ideas magically reveal themselves!

Take note

When someone tells a story that sparks a gift idea, I try to record it right away. My favorite way to do this is by adding it to my “Gift ideas” Amazon shopping list. Even if I don’t end up buying it on Amazon (a habit I’m trying to break), when shopping time comes around, having it in that list will trigger my memory. 

Sometimes I send myself an email with a vague idea, like, “something for their trip to Disney World.”

If I can, I will buy it or start working on it at the next opportunity.

A little inspiration

Recently I asked some of my friends, “What’s the best gift you ever received, and why?” 

Every one of their stories gave me little goosebumps of joy, and I even teared up a bit. 

I looked for a common thread, and my friend Sandy put it perfectly: “The best gifts in my mind are the unexpected things that send the message ‘I see you’ or ‘I'm paying attention’ ... like when a friend drops off a card and a little plant or chocolate when I'm having a rough week or my hubs or boys pick up on something that came up in casual conversation and make it happen.”

Without further ado, here are my favorites. 

“The Christmas of my freshman year in college, my oldest brother (9 years older) burned me the 10 albums he wished he had when he was a freshman and designed all the cover art himself. It was the best because he put a lot of thought and time into it and having your big brother introduce you to bands is inherently cool. They're at my mom's house, but I plan to grab all the cover art next time I'm there and frame it.”
— Molly B., New York, NY

“It was almost a generic gift bag from the mom of a friend, but it was filled with the best stuff- A great paperback book, a box of fancy tea, a new Christmas ornament, and a small box of really good chocolate. It may have been so awesome because I wasn’t expecting the gift and it was filled with all of my favorite things.”
— Tracy M., Milton, MA

“This little bill sorter. As a kid I always would run into my grandparent's bedroom when we'd visit to see if ‘the cat was still there.’ When they got older, I told my parents that when they passed, the only thing I wanted was ‘the cat.’ Well, after they both passed away, my Aunt cleared out their apartment and threw it out. She didn't know how much it meant to me. I was heartbroken. Turns out, my Dad spent the next 5 years on the internet off and on trying to find an exact replica. I had no idea, and one Christmas about 6 years ago, he said ‘there's one more gift for you.’ And, it was the cat!!! I burst into tears as soon as I pulled back the tissue paper and saw a glimpse of the wires. I knew instantly what it was!!”
— Michelle W., Reading, PA

“[My husband] writes me a letter each Christmas as my present. It is a Top 10 of things we did in the previous year. This means so much more than an actual gift to me. He has been doing this for almost 20 years.”
— Tracey R., Oro Valley, AZ

“When I was in middle school my brother left for college and I missed him terribly. I made him peanut butter cookies with the fork marks and mailed them in a care package with a yellow post it note saying I missed him. 6 years later I was living in London doing an internship and I had a visitor. My brother’s friend was in London for work and delivered a box of homemade peanut butter cookies with the same post it note and on the back it said miss you too... Totally unexpected and he kept that post it note for 6 years.”
— Sue O., Northborough, MA

“My boys composed and sang a song for me, a parody, for my birthday. They’d done it for 10 years for my husband, with my prodding. This year, under quarantine, they did this on their own, surprising me.”
— Nivi E., Cleveland, OH

“My brother (10 years older) gave me a little gold Woodstock charm, because I had given him a plastic one to put on his desk to help him with exams in college. I also still have letters from Santa in his handwriting.”
— Jane F., Boston, MA

“When I was in sixth grade my grandparents bought my sister and I each a plane ticket to go to Disneyland with our cousins out west. I had never been on a plane before and that was exciting enough... but then they also bought my mom a ticket and she didn’t know she was going too and she cried and to this day it’s the best gift I have ever been given or seen given.”
— Sarah D., Pembroke, MA

What made these gifts so special?

What common themes do you hear in these stories? Why did the recipients love them so much?

The gifts were unexpected, the giver invested quite a bit of time, and they showed that the giver really listened to figure out what would make the recipient feel extra special.

While you can pay attention all year long in preparation for the holidays, it’s never too late to start! Listen closely over the next few weeks and you, too, can develop the gift of finding just the right gift.

Happy holidays!

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