When the Christmas Gift List Becomes a Hostage Situation and Stops Feeling Like Giving

By Glen Maylone

At some point in adulthood, you wake up one morning, look at your bank account, look at your Amazon cart, and realize something profound:

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You are buying Christmas gifts for people you might not have had a real conversation with since pay phones were a thing.

And that’s when the question quietly creeps in: “When do we stop buying Christmas presents for certain people?”

Not the kids. Not Grandma. Certain people, are permanent on the love, based gift giving list of course.

I’m talking about the extended cast — the in-laws, the siblings, the cousins, the once-removed, the twice-estranged, the people who only text you once a year and it’s either:

“Merry Christmas!! ❤️🎄❤️”

or

“New phone who dis?”

Not that you don't love these people too, and that is where it gets tricky doesn't it.

Every December, like clockwork, I find myself asking the same thing:

How did this become my fiscal responsibility?

How did I become "the president for life" of the: Annual Family Gift Club?

At some point I inherited: leading the trips to the store, or doing amazon searches until my fingers ache and my bank account screams,

"Please just stop".

This came up recently when my wife and I were talking about Christmas plans.

First it was the travel, where are we going, when, conversations.

Then she looked at me — calm, practical, unbothered — and took the conversation 90 degrees by saying:

“I think it’s time we narrow gifts down, maybe just the grandchildren and nephew.”

I stopped. Blinked.

Waited for the punchline.

Because for years, I’ve been buying Christmas gifts for what feels like the entire extended branch of the family tree — parents, siblings, partners, assorted relatives, and occasionally someone who happened to be standing nearby when we walked in.

(I think the pizza deliver guy may have stumbled into a gift card once).

At this point it feels like I’ve basically been running a holiday foreign aid program, but one without any matching contributions.

So, when she said, “maybe we just focus on” I had four immediate reactions:

Relief (“Finally, the list is being downsized.”)

Surprise (“We can just… stop?”)

Guilt (“Is that even allowed? Will someone revoke my Christmas privileges.

Then optimism: maybe I will get paroled from the fruitcake list?

When Tradition Turns into Obligation

Here’s the thing:

Gift-giving starts as a sweet gesture.

For me it starts with doing something for people out of love.

Then it morphs into a tradition.

Then it quietly evolves into an expectation, and one that is based on your ability to give, not the reason you give.

And eventually it hardens into an obligation.

Nobody talks about it.

But everyone feels it.

You don’t want to disappoint anyone.

You don’t want to look cheap.

You don’t want to be the one who breaks the unspoken pact of “everyone buys everyone something forever.”

But buying gifts for adults gets tricky because… well… adults buy what they want anyway.

(And if you buy what they need instead, well, a gift card for an oil change doesn't scream Peace on Earth, Good Will to Men)

Which means Christmas gifting becomes a strange annual exchange of:

candles

socks

gift cards

novelty mugs

and items no one asked for but everyone politely smiles at.

At some point, you start to wonder if we’re all just swapping stuff for no reason other than inertia.

The Other Factors

The Culture Factor In many families is another thing:

Especially those with strong cultural or generational traditions — gift-giving is tightly woven with respect, appreciation, and togetherness.

Which means scaling back isn’t something you do lightly.

It’s wrapped in history.

Expectation.

And a little bit of holiday emotion.

But even long-standing traditions can be revisited.

And my wife, wonderfully level-headed as always, finally said the thing that needed saying:

“Maybe it’s okay to simplify.”

She’s right. (shhh, don't tell her I said that)

The Turning Point

Look, I’m someplace in my fifties.

"Maybe closer to 60 than I like to admit, but the mirror reminds me of daily."

I’m officially in the phase of life where time, energy, and attention are far more valuable than wrapping paper and last-minute Amazon deliveries.

And if I’m honest?

The people who truly light up — who really, genuinely feel the magic — are the children.

Everyone else?

They’re fine.

They smile, they say thank you, they add it to the pile, and a week later they can’t remember who gave them what.

But the children?

They remember. They cherish.

They radiate joy.

They jump up and down.

They call you afterward.

They beam.

That’s the ROI I’m after.

Genuine happiness in return for what is genuinely given out of love.

Back to the adults:

So, When Do You Stop?

Here’s the conclusion I’ve come to:

You stop when it stops making sense.

You stop when it becomes burden instead of joy.

You stop when the tradition drifts away from the relationship.

You stop when the list has momentum but no meaning.

And you stop when someone finally says: “It’s time.”

The New Rule in Our House

Our updated holiday protocol is beautifully simple:

🎁 Kids get gifts.

🎁 Adults get love, time, and food.

🎁 Everyone gets peace of mind.

And honestly?

It feels right.

It feels sane.

It feels like the beginning of a clearer, healthier tradition — one based on connection rather than obligation.

Because Christmas should be about joy, not inventory management.

If You’re Reading This:

Here’s Your Permission Slip:

If you’ve been quietly wondering whether it’s time to shrink your holiday gift list.

Here is your official Fed to Freedom note:

You are allowed to simplify.

You are allowed to protect your energy.

You are allowed to redirect generosity where it matters most.

Traditions evolve.

Families change.

So can you.

And sometimes the greatest gift you can give yourself — and everyone else — is to stop buying mountains of things no one needs and focus on the relationships that truly matter.

Love, Family, and Friendship!

I wrote this thinking how truly blessed I am!

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