Gift Giving: Nightmare Difficulty

So I have some impossible people to buy presents for (e.g. my parents are always impossible) and I need some advice, or at least some commiseration.

What are some of the best gifts you've given or received? Who are your impossible people to buy for? Do you have any go-to gift strategies? Does this time of year make you want to drink as much as me?

Life altering Maryland Smith Island Cake.

I've never won a penny on scratch off lottery tickets, but I got about $70 worth for my brother in law when I got him for our family gift exchange. He had a blast scratching them off with the grandkids and actually won $450.

I try to identify objects that everyone uses but usually buy on the cheap. Two recent successes were a maglite xl 200 for a relative that was using a crappy flashlight to walk his dog at night and a Tempurpedic pillow for a someone who was pillow stacking at night.

Maglite: http://maglite.com/shop/maglite-xl20...

Pillow: https://www.amazon.com/Tempur-Pedic-...

Since my family all live with or near my folks I find that sending one of the these early December gets me off the hook for any deficits in individual gifts.

Come to think of it, the best solution is to get these people off of your Christmas list. I haven't bought or received birthday or Christmas gifts for my parents since I was 20. On my wife's side we have a gift exchange so I only have to get one gift other than my wife.

I usually have a difficult time buying for my folks, but I have since come across Coffeereview.com and will be purchasing some gourmet coffee for them this year. They usually buy decent coffee, but don't really splurge on something more extravagant, that's where I come in this year.

I don't have any specific items in mind, but when I have to buy something for "the person who has everything", I try to figure out what they like but would feel guilty about buying for themself. My best friend doesn't need anything, but he has 4 kids and I know he wouldn't buy a nice bottle of scotch for himself because he'd rather spend it on his family. That's where friends come in.

Trophy Husband wrote:

Come to think of it, the best solution is to get these people off of your Christmas list. I haven't bought or received birthday or Christmas gifts for my parents since I was 20. On my wife's side we have a gift exchange so I only have to get one gift other than my wife.

Late to the thread, but this strategy has been a game changer.

My family has also experimented with doing charity donations in the name of your giftee. Charities where you sponsor a child and get updates throughout the year are perfect for this. Some of the micro loan charities work well too. It does take a little research to avoid scams.

Hmm. Makes me want to give to Planned Parenthood on behalf of my Trump voting friend. Hmm...

How do you do that, without their finding out? Asking for a friend...