Their sock drawer is overflowing; they have a well-stocked kitchen including glassware, platters and yes, even linens. They don’t collect anything, never wear costume jewellery and read only e-Books and magazines.

So what do you buy your Secret Santa who appears to have everything? Whether it’s a partner, relative or colleague, this typical know-it-all can be hard to impress.

The usual suspects run through your head, but you really want to give them something unexpected.

Last year, I was faced with this dilemma. I was buying for, to be blunt, a picky artist and minimalist who knows what she likes. I was stumped and felt constrained by our $25 limit but I set out to do the best I could and I started as early as possible.

Soon, it came to me. A conversation we’d shared about those decorative, hand-blown eggs. Pysanky. A few minutes later I was on Etsy and I’d located, for $19 all in, a set of five handmade pysankystraight from Poland. I thought about it overnight and bought them the next morning; they were just the mix of quirky and unique I was looking for.

It’s easy in hindsight to see how simple it was to please myself and the minimalist artist, but there’s a lesson there — pay attention to random conversations and habits. You never know when that one-liner from a fun office event will be needed.

My friend didn’t know she wanted the eggs, but as an artist, I knew she’d appreciate the workmanship and their cheery colours.

My second key to success? Starting the hunt early and taking notes. I keep a running list of ideas on my phone and regularly bookmark trendy websites I think could be useful when the holidays roll around. It’s a simple, non-committal way to track those random conversations and strokes of gift-giving genius.

If you don’t have the luxury of time, another trick that keeps both gift-giving fun and challenging, is to dream up a theme. Perhaps you decide to give gifts that are 100 per cent locally made, or maybe all of your gifts are fairly traded and made by global artisans; or maybe you want to share your love of music, art or film with those closest to you. Whatever you choose, stick to it, and enjoy the challenge. It may even give you a conversation starter at the office holiday party.

Got a doozy on your to-buy for list? Try these ideas:

  • Theme it
  • Start as soon as you can and take notes; guaranteed there will be some surprises on that list you started more than a month ago.
  • Take a chance and buy those decorative eggs or,
  • Pay it forward and give the person an experience; hey, even an unexpected night at the movies thanks to a gift card is achievable.
  • Plan an outing or event together. Does your friend like to work out? Try out a new gym or studio together. A fan of the great outdoors? Rent some snowshoes and get out there.