You Shouldn't Have
I polled my friends For the thoughts that almost counted: My Gift-Giving Hits and Misses
Not to be a Scrooge, but one in five presents will end up in a landfill.
Tim Hartford, a podcaster for The Financial Times, did a fascinating episode on an economic phenomenon he calls, “The Deadweight Loss of Christmas."
The idea is simple: a staggering number of gifts miss the mark. The person who smiled and said thank you doesn’t actually want their present, so it either ends up in the trash or the junk drawer, collecting dust and taking up space for years.
And yet, I’d still rather “guess and gift” than hand over cash, the king of practicality.
For me, a gift is a way to say, I see you. It’s a physical manifestation of care, a summation of all the little things I’ve noticed about you: what you love, what you lack, what makes you laugh. I love wrapping up that insight and gently putting a bow on it. I love watching for the moment of recognition, the spark in someone’s eyes when they feel seen.
Scrolling through my Substack feed full of Gift Guides this season, I’m not alone. Cash is the equivalent of writing “Have a nice summer!” in someone’s yearbook.
But I had a nagging voice in the back of my head: Am I as good at gifting as I think I am? Is it like driving where everyone assumes they’re above average, but the math doesn’t add up? So I asked my friends.
Each shared their best gift; only one was brave enough to confess the worst. But once the floodgates opened, the stories came pouring out—epic highs and lows courtesy of mothers-in-law, boyfriends, girlfriends, and grandparents.
Before I pat myself on the back, let’s acknowledge the possibility that my worst attempts were so epically awful they’ve been repressed as a trauma response. Either way, it was a fun ride.
The Worst - Making Coal Look Like a Luxury Item
1. Gifts That Create a Burden
“The wreath from your Mom. It required me to find a place and hang it up. I didn’t want to damage my door with a nail, and it ended up being a burden rather than a gift. The worst kind of gifts are the ones that require you to do a lot of work.”
"He bought me tickets for Christmas to see Wicked, which I had been dying to see. But it was in another city. I had to plan and pay for the entire trip, including the hotel and train tickets.”
“My boyfriend gave me this stupid plant I had to take care of. Luckily, we broke up before I had to tell him I killed it.”
2. Gifts That Feel Impersonal or Thoughtless
“My mother-in-law is the worst gift giver (Bless Her Heart): Random games we’ve never heard of, coffee books that mean nothing to us. Just stuff.”
“A small cutting board with my last name and the year on it.”
“A “Favorite Daughter” shirt in a Kid’s Size Medium…it could barely fit over my head.”
“My Sister gave me a used hairbrush. She forgot to give me a gift and thought I wouldn’t notice it was the same hairbrush my Mom had given each of us for Easter. It still had her hair on it.”
3. Gifts That Feel Like Criticism or Insults
“My ex gave me workout clothes. I didn’t ask for them, so it just felt like a hint that I needed to get in shape. I started crying.”
“When I was a kid, my parents gave me a computer. But it could only do math. It was a trick. And I’ve hated math ever since.”
Gag Gifts That Go Too Far
“Gas X. My mom bought it for me as a joke, but it was when I was just a kid, and I opened it in front of all my friends. I was super embarrassed.”
“A large box flagged as pornographic material that I had to pick up from the front desk of my new building.”
Gifts that are for the Giver
“My fucking husband got me fucking Tupperware because ‘I like to cook."
“A mattress cover from my boyfriend. He didn’t like the bed at my apartment and constantly complained about it. It was my big Christmas gift that year, and I still remember the exact moment I opened it. It was also Memory Foam, which he knows I don’t care for".
And:
The Best - Step Aside Santa
Gifts that Support Hobbies and Passions
“The surfing lesson for my Birthday. It was really fun to do it together and then spend the day, and you got me lunch too. It was thoughtful and fun, and it even introduced me to the surf coach who totally elevated my surfing. I got so better from working with him so it really impacted me in a big way in something I love.”
“We were talking about vision boards, and you sent me two cool curated inspiration boxes from Etsy to help put my boards together!”
2. Gifts That Make Someone Feel Seen and Understood
“The socks with my cat’s face screen-printed on them. They were SO unexpected and very unique and also practical!”
“The best was when my husband got me like an inch of land at a Scottish castle so I could officially be a Lady, just like I’ve always dreamed.”
“A Caraway cook set from my boyfriend when we were still living separately. I had only mentioned once in passing that I really wanted it (and planned to get it for myself), but then he remembered!”
“The stuffed bear you made me. Obviously, it’s not hard to know that I like bears, but you put so much energy into it in swear words from stabbing yourself with the needle and time and all sorts of frustration. It’s hard to give meaningful gifts nowadays, especially when we have so much abundance, and you can get so much off Amazon. It was thoughtful, personal, and different. Your time and energy were the hardest for you to give, so it made it that much more valuable; it’s all about bridging that gap whenever you have an opportunity.”
Gifts that Solve a Problem
“The fold-up cart you got me for my car when I constantly lugged belongings back and forth between my two places. It’s brought unaccountable moments of gratitude. This cart is so convenient, sturdy, and storable. It was a problem that I was willing to live with, but you solved it for me.”
“A hook next to my bed to hang my eye mask on. It’s not even expensive, but I kept losing my mask and then each night I would have to look for it. And now I finally have a place for it!”
And sometimes you just know:
“The best gift is a nice Tea Kettle.”
“All my gifts have been bomb. Even when my Grandma gave me six cans of jellied cranberry cans or cans of black olives, or a large five-pound box of Red Vines, it was always in theme and followed by another gift.”
Comedy aside, reflecting on these examples brought me back to my Portuguese family, who could rival accountants in their meticulous tracking of gifts. They always painstakingly made sure the gifts they gave matched the last gift they’d received from someone, even going so far as to look up the prices online or in the store.
Growing up, I found this so embarrassing. Isn’t the point of giving to be generous? Who cares if your gift ends up being a little bigger? It was so tight-fisted.
But when I toured the Hawaiian sugar plantation where my family once worked, I saw the little handwritten “gift ledgers” they kept in the early 1900s.
It hit me then where this mindset comes from - a history of poverty.
One of my family’s Christmas traditions is to tuck an apple and an orange into each child’s stocking. Historically, these two fruits were a Christmas gift each year from the Hawaiian Sugar Barons to the children of the plantation. Kids were actually excited to get them. For the adults, it symbolized our roots: a history of hard work and poverty, and an appreciation for leaving it all behind. For the kids…my apple and orange would quickly find their way back into the kitchen fruit bowl while I set up my new PlayStation.
When every dollar counts and every meal is hard-earned, generosity isn’t about showing off—it’s about survival. A $5 loan scribbled into a little ledger wasn’t just a kindness; it was a lifeline, with the quiet understanding that when hard times inevitably came for you, that $5 would return in kind.
Gifts, even the smallest ones, were a way to honor relationships with balance, taking care no one felt indebted or undervalued.
In times of abundance, the meaning shifts. It’s all about the recognition and understanding that person feels when they open the gift and think: I am seen.
What are some of your best and worst gifts? I would love to know in the comments.
I’ll be back with regularly scheduled programming for my next article. I’m excited to explore clap-back culture, forgiveness, and grace in online spaces.
Here’s a sneak peek: I’ll be sharing an interview with a close friend, a Christian from the Bible Belt South who, as a straight ally, co-led Creative Artists Agency’s (CAA) LGBTQ coalition.
“My mom modeled a “love first” posture, volunteering at Mama’s Kitchen for people with HIV and AIDS, so I connected with the LGBTQ community from a young age without even realizing there was supposed friction.”
We had a great conversation about how Cancel Culture often reduces people to data points instead of acknowledging them as complex, multifaceted stories. I’m so excited to share more.
Knowing you’ve spent your time reading this is the best gift I could ask for. If you enjoyed it, please like, share, or comment - it really makes a difference. Thank you!
I’ve discovered that gift-giving for the sake of it is just not my thing. I’m happy to give to people and organizations in need but just exchanging gifts with people who I know don’t need anything…seems kinda pointless…?
But my mom LOVES gift giving. It’s how she shows love. So I know better than to ask her to stop getting me gifts.
I focus on giving consumables. One year when I was a cashier at a fancy grocery store, I made my parents a basket of snacks popular with the Real Housewives crowd.
One year I baked apple cinnamon bread for everyone. This year I went to a local farmer’s market and got some unique food items I knew they would want to try.
I’ve bought a lot of Cameo videos over the last 3 years. Recipients don’t always know what to do with them or how to react but at least I know the money went straight to an artist or charity.
The high-effort sentimental gifts tend to go over well. A few years ago I spent a lot of time interviewing older family members about my great-grandmother. She was a legend and universally loved. I typed out all the interviews and put them in a small book and my whole family thought it was really special. My only
regret is I wish I had done more interviews.
My husband and I have a close friend whose Dad loves to tell stories and is getting up in years. We secretly bought his dad a Storyworth subscription and his dad wrote a story from his life every week for almost a year. Putting that book in our friend’s hands and seeing his face was pure magic. A top 10 life experience.
Me and my wife often have gifted each other concert tickets. We go halfers on any required travel and we both have a good time together.
With Christmas, birthday and valentines coming close together before a little break to anniversary I do a bunch of shopping and then decide what goes for which holiday.
One last quirk. My wife doesn't seem to stress about who spent more but she counts the number of presents we each open trying to keep them even.
Pro trip if your wife's birthday is Feb 16 or really if a birthday is near a holiday DO NOT combine presents. I got this instruction very early on and have kept to it.