For me, every year, I find Dad is the hardest to pick out gifts for. For Mom and my brother I usually get books (or occasionally films), but Dad's eyesight is so bad that he can't read recreationally anymore (he used to love to). Audiobooks are more viable now, though those run a lot pricier.
My sister. I would rather not buy for her at all but as I buy for my mother and brother I feel I have to buy for her as well. I have no idea what her tastes really are as we only see each other a couple of times a year.
We do Secret Santa every year, so I only have to buy gifts for one person. I have my aunt this year, and normally she would be easy to buy for, but apparently health reasons have stopped her from drinking coffee and eating chocolate. I don't think she has any other hobbies!
Apparently I am the hardest to buy for, but I imagine that'd due to proximity: my family are all in Seattle and I'm in NYC. The only person for whom I really struggle to find the right gift is my best friend. It's odd, because I know her better than anybody, but I can never seem to find the right thing. She has the same difficulty with me.
My best friend and I (well, all of my friends, really) don't exchange gifts. We just buy each other beers when we go out.
Definitely my mom. She likes to read, but that's about it. She doesn't really like movies or TV, she's allergic to flowers AND chocolate, in fact she really can't stand sweets at all, and she doesn't really have any major hobbies that I'm aware of. She works part time and raises four kids so I suppose she doesn't have much time for them. She also hates girly stuff, so getting her bath stuff or scented candles is definitely out. She is not the sentimental type (and neither am I). Her birthday and Christmas are right next to each other, so I usually buy a book for one of them but can never think of what to do for the second one.
My Dad, before his Alzheimer's took over. He hated almost everything, and made you feel like crap for daring to buy him a gift. Now my sister has that role. She always says, "Oh, don't buy me anything," but we all know damn well that there'd be hell to pay if we didn't. And when we do buy her something, she complains and rolls her eyes---often right in front of you. Now I don't even care anymore. I get her something, and if she doesn't like it, she can return it. This year, her ex-boyfriend---who has done a lot to help look after my Dad---is joining us for Christmas. I know him, but not well. I have no idea what to buy a 45 year old single Dad. He has his own home theater business, and he's doing relatively well. He just got a puppy--maybe some stuff for his new dog? I have no idea.
For me the hardest are job related. Where I worked the longest, the supervisors generally gave Christmas gifts to the people they supervised. It was really hard to find something interesting for each person w/o getting too personal (or expensive).
Have you considered getting your dad an MP3 player so you can download audiobooks from someplace like Audible.com? My hubby is difficult to buy for because he buys stuff he's interested in throughout the year. This year, I've bought him an iPad because he'd talked himself out of getting one. But every other gadget, he already has. My parents, as a pair, are hard because they're old and don't actually need to accumulate much else. It's a challenge to get them something useful that's not going to take up space in their little house.
It varies. Some years I get inspiration and have great ideas for everyone. Others, like this year, I have no clue for anyone. I'll probably just buy booze for my parents. No idea for my brother and sister-in-law. I don't usually buy gifts for friends, unless it's in a Secret Santa type thing. Otherwise if you buy for one friend it tends to start a chain reaction of obligation shopping for other friends, to avoid hurt feelings...
My family doesn't do presents anymore, I only buy a present for my nephews. I find them quite hard to buy for because I don't just want to get them some generic crappy toy that will wind up in a pile of other generic crappy toys. I like to find them something that they will treasure or that will help them towards specific interests, at least until they break or destroy it.
The hardest in the last years was my grandfather, but he died this year. So now I´d say the hardest is my father. TerokNor
All of my friends who coincidentally are girls. How do I give somebody a Christmas present without giving off too deep of a signal? Ira, I give him a pocket knife or something and he's like "oh cool, thanks bro" and thinks nothing of it. If I buy Jesse a package of drawing pencils or Heather a How to Learn Japanese CD, on the other hand, they think I'm ripping my soul for them when I'm just being a good friend and then there's my ex... would it be at all awkward if I gave her something? Would her new boyfriend kick my arse, would she eat it and vomit the pieces into my eye? (I really was a bastard to her and I still feel horrible for it. Thank God I've learned my lesson)
If you're still friends, it might be okay, especially if you're both part of a social group where everybody exchanges gifts. Just don't make it anything too personal or expensive. But, otherwise, yes, it will be will be awkward; personally, I would skip it. BTW, if you're looking at this possible Christmas gift as a substitute for an apology you never made, it might be better to be direct: send her a Christmas card (either e- or paper) w/ a note of apology.
I like that idea! Also maybe a book about the breed (if it is a purebred), or some other kind of book relating to dogs? (BTW, he sounds like a really nice guy.) Until recently, i would say it would have been my mother. She and i have extremely different taste on everything! Nowadays, the years we don't spend Christmas together i just have something sent to her (she is in Florida, i'm in NY) from a food company. I particularly like Edible Arrangements (she seems to love it when i send her those). Nowadays (well, always, he was a tie with my mother), my husband is impossible to buy for.
My dad is always hard to buy for. We live on different continents now so we don't exchange gifts, thankfully, but I have many memories of thinking what the heck to buy an "old man" (he was 42 when I was born) who is ultra-religious and doesn't really have any hobbies. In fact, my entire family struggles with buying gifts for my dad, though he appreciates most things, even if they are useless to him.
He IS an extremely nice guy---which is why we're glad he's my sister's EX-boyfriend. We were very glad when they split up. She's incredibly abusive and manipulative; she goes through men like a shark in chummed waters. Yet, she still gets them to do things for her, like fix her plumbing or babysit her son--after she's thrown them out. It's amazing. I like him a lot more than I like her. If it weren't for my nephew, I'd have nothing to do with her. I joked with him at Thanksgiving that I was going to get him a subscription to E-Harmony (he laughed), but I couldn't really do that to him in front of everyone. I think I might go down to PetSmart and see if they have something neat for his new dog.
No one in my family is hard for me to buy for. I always buy gift cards, to places I know they go, unless they tell me exactly what they want.
I don't have any problems finding stuff to buy for folks since I only give presents to people I'm close with and therefore know their tastes well.