I always have the same problem when "gift-giving" situations arise.
First, I'm pretty broke. I know, I know, stunning... an artist without money to spend. News at 11. But this has been true for years. Decades now, I suppose. Money goes to rent, to family, to random chance (vet bills, car breakdowns, replacement heaters, and so on), and the few scrabbled pennies I put aside for "savings" are vapourized instantly as I try to buy stuff for people I love.
Second, I'm really bad at getting gifts. I think this comes down to an inability to pick up on clues. I'm pretty oblivious, even at the best of times. I tend to try to just ask people what they want and then get that: This makes me a mediocre giver of gifts at best, since the good ones (like my buddy Alex) are almost psychic in their ability to manifest strange hints into concrete gifts.
Oh well. I've purchased a few things my family have stated they want: I've dodged getting gifts for most of my closest friends by stating monetary concerns (and instead focused on spending time together, where and when possible!), and I'm going to be leaving it at that.
Anyway, thankfully this only happens a few times a year (Winter Festivals, and a few scattered birthdays for my nearest and dearest), so it will be over soon.