The Best (and Worst!) of Secret Santa

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This Christmas, readers share their most memorable (thoughtful to strangest) Secret Santa gifts.

From a handwritten letter to tea-stained mugs, here is what they had to say about the art of anonymous gifting.

The annual ritual of Secret Santa is far more than a simple holiday tradition; it's a high-stakes social litmus test.

At its best, it is a heartwarming display of attentiveness - proving that a colleague or friend has truly been listening.

At its worst, it is a frantic, last-minute dash that results in "questionable" smells and awkward handovers.

Whether it's a moka pot that fuels a morning or a rubber lizard that fuels a nightmare, the consensus is clear: the most memorable gifts are the ones that prove you were seen.

The value of a gift rarely lies in its price tag, but rather in the "observational bridge" between the giver and the receiver.

From sentimental letters that capture fading moments to "reality check" calendars that call out our worst habits, these stories from four professionals explore the delicate art of gifting - and the hilarity that ensues when it goes south.

The curator of rituals

"Secret Santa has a funny way of showing how well people really know you," poses design and art manager Ifra Ali.

For someone, whose career is built on aesthetic and intentionality, the "perfect" gift wasn't about the price tag, but the lifestyle it acknowledged.

She fondly recalls, "The most thoughtful gift I've ever received was gourmet coffee paired with a moka pot, along with a handwritten note. Anyone who knows me knows how serious I am about my coffee and my caffeine. On its own, the gift wasn't extravagant, but the note mentioned small things I had casually spoken about, like how coffee instantly improves my mood and how I enjoy slow, intentional mornings. That attention to detail made it feel incredibly personal."

However, Ali notes that without that observational bridge, gifting can feel dissonant.

"Then there was the not-so-great gift. I once received a wind chime. While it may sound thoughtful in theory, it felt completely random for me. I don't really enjoy constant background noise, so my immediate reaction was a confused smile and a quick mental calculation of where it would even go. That contrast is what makes Secret Santa interesting. When someone really thinks about you, even a simple gift can feel special. And when they don't, it becomes a funny story you end up telling later."

The seeker of sentiments

In the fast-paced world of finance, banker Sneha Sharma finds value in the things that cannot be digitised.

She emphasises that in an era of instant gratification, effort is the true currency, "At this stage of life, you understand how quickly conversations fade and messages disappear. That's what makes a handwritten letter feel so rare. I once received one recalling one specific moment shared between two people, and it carried a quiet, lasting power. It doesn't try to impress or perform, yet it feels deeply personal. Someone noticed that moment when it happened, remembered it, and chose to hold on to it."

But the banker's eye for detail can be a double-edged sword when a gift lacks sincerity.

She describes a jarring experience, "On the other hand, I once received a gift that made me pause: a mug that was very clearly used. It wasn't broken, but it had faint tea stains along the rim and a slightly faded design from repeated washes. The box looked new, which somehow made it worse, as if effort had gone into disguising its past life. There was no card, no explanation, just an awkward handover. Gifting is about thought and intention; this gift didn't have any, and that absence was impossible to ignore."

The practical dreamer

For Disha Sharma, a successful gift sits at the intersection of utility and nostalgia.

As a PR professional, she understands the power of a good ‘hook,' and her favourite gift had exactly that - a mix of high-function and high-sentiment.

"The most thoughtful gift I ever opened was a travel pouch, a Cinderella-themed stationery set, and a handwritten note. At the time, I was about to travel, so the pouch felt perfectly timed. But what really stood out was the stationery. It wasn't just about my love for the character; it felt like a gentle reminder that somewhere inside all of us, there's still a small child who believes in a little magic," she says.

When asked about the strangest gift she received, she shares an instance her Secret Santa failed to deliver terribly, "However, I've also been on the receiving end of a 'panic buy.' I once received a black hoodie that practically announced itself as a last-minute roadside purchase. The fabric felt oddly worn, the fit was strange, and there was a very distinct, slightly questionable smell. I smiled, of course, but internally I was trying to guess its backstory. When something is a re-gift or a last-minute buy, it shows. Instantly."

The good sport

Dhairya Sharma views Secret Santa through the lens of relationship dynamics - sometimes it's a tribute, and sometimes it's a prank.

"My most unforgettable Secret Santa happened with my cousins," Sharma reveals.

"I opened a box casually, and right on top was a very realistic rubber lizard. I'm extremely scared of lizards, so I panicked instantly - I screamed, dropped the box, and jumped back. My cousins were all recording and laughing; it was a prank because they knew about my fear. It was completely useless as a gift, but it turned into a hilarious, creepy memory," he notes how an eerie prank can become a lifelong memory.

Shifting from family chaos to corporate life, Sharma admits that Secret Santa can also serve as a mirror to our own flaws. "I also once received a gift that was a bit of a reality check. At a workplace exchange, I received a desk calendar with a note that said, 'Let's actually meet this time.' I have a habit of cancelling plans at the last minute because after work, I often feel like I should just run straight home. The room went quiet, then everyone laughed because it was true. Now that the calendar sits on my desk and reminds me to show up more often."

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