Thoughtful Gifts for the Hard to Buy For

I'd already written up a gift guide for hard to buy for moms, then realized, my ideas are actually helpful for everyone. I just happen to have a HTBF mother (my dad is the total opposite), so I have a couple of decades of figuring out what to buy for her under my belt. Not that the road hasn't been paved with last minute dvds and random tchotchkes,  but I think I've come a long way as a gifter. So here in time for Black Friday, are my tips for gift giving, for the hard to buy for in your life.

1. Just ask them what they want. Yes, this is glaringly obvious. No, I don't mean it at all in a smart assy way. I realize that sometimes, we so want to surprise loved ones with spectacular gifts, that we overwhelm ourselves trying to find the perfect one. Then, we wind up scrambling last minute and wind up with something that may not be anywhere near what we'd intended. So, instead of trying to be sly, just ask. If you want to surprise them (and who doesn't, really?) discuss it in a way that is less like trying to suss out info, and more like a general conversation. Something like "I've always wanted the Charmkins windmill, but ebay is ridiculous. How about you?" 
2. Set up a family wishlist. This is especially helpful for families with younger kids/teens at home, or families who do a name/gift exchange. Amazon is a great option for general wishlists (you can even organize items by how badly you want them), and if you hate being out and about during the holiday season, you can shop right from home. Elfster is a secret Santa organizer site that is simple to use and can be linked to your Facebook account. You simply invite family/friends to the exchange, they answer anonymously asked questions and/or fill out a wishlist, names are drawn and gifts exchanged. It's Secret Santa without the hassle.
3. Answer these questions- What do they hate to do, what do they love to do, what have they always wanted to try? My mother's lone request all these years has been for a clean house. There are several reasons why that never happens (she refuses to do it herself, chief among them.) So I say, if you want to know what a person truly wants, answer these three questions. Delving further into things, knowing what they value most- services, experiences, or things- is also key. So if your mother hates cleaning, is always complaining about it, pay for a maid service. If she is unwilling to allow strangers into her home, volunteer to do it yourself (and actually DO it, don't say you will then reneg because you're broke. Or cheap.) If someone is interested in developing a skill, experiencing a once in a lifetime event, or just would like a weekend away (if your budget allows), figure that thing out and make it happen. This one also allows for time spent with loved ones- which is important to many, and free.
4. Let gift cards supplement, not supply. I am a fan of gift cards. As someone who has never been good at on command wish listing (and who is prone to whims), they take the headache out of things. But they can be boring, and I have heard a few people complain that it's no fun to buy them. With that in mind, I say let a gift card add to the overall gift, and not be the entire gift. If your sister hangs out at the library, figure out her favorite authors or genres, buy her a book- and tuck in a B&N or Starbucks card. If your brother loves cooking outdoors, get him a cast iron cookware set and a card for Bass Pro Shops, Cabela's or Lowes. If your parents never make time for themselves, buy them an outfit and add a certificate to their favorite restaurant. You can still give gift cards, but putting a little more thought into a gift is always appreciated.
5. Give of yourself. This one kind of ties into #3, but with a more DIY angle. If you are a talented photographer, graphic designer, knitter, baker, put those skills to use! If you are good with editing and design software and know a couple of new parents, design a birth announcement, print it on heavy card stock and have it framed (I've done a couple using Picasa, and I've seen others on Etsy.) If you are handy with a camera, take a family portrait or offer to photograph your nieces, nephews, cats-in-law, etc. Cook a gourmet meal, offer to babysit, wherever you see a need you could fill, offer to do that, and do it.
6. DIY Gift baskets. No matter what you could offer to do for some people, there will always be those that prefer things over all. This is ok! There's a reason gift sets abound during the holidays. They are easy. Many have brand recognition. And some have hefty price tags. If you have many to buy for on a limited budget, try buying mini sets and breaking them up. Stores like Bath and Body Works, and many cosmetics brands offer these kinds of sets every year. If you have several teen girls to buy for (or even older women! as long as they like health and beauty products, this will please), buy several sets or travel sized products, a cosmetics bag (Wal Mart and Target have many affordable and stylish options), and round it out with little things like small candles, chocolates (or other candies) and nail polish. You could even do a more specific set, such as a pampering routine, mani-pedis, skincare, hair styling. I suppose girls can be easy to buy for :) If you have more guys to gift, movies, video games, gadget accessories (who isn't always looking for a charger cord?!), and even grooming kits are good ideas. My assumption is that you probably know the people you're buying for well enough to know what they are into. So if you have a brother, cousin or nephew who is more into cooking than power tools, get him a cookbook and some kitchen tools. And stuff em in a crockpot or a heavy-duty enameled cast iron pot that will last them forever. The options are pretty much endless here. 
7. Big Ticket Ideas. If your dad's dream has always been to restore an old car, but he never looks for one, get yourself online and look for one. Between Freecycle, Craigslist, and local classifieds, you might just luck up and find something that someone wants to get rid of cheap (or maybe free! My brother was once given a 1950 Ford car. You just never know unless you look!) If you have a big or even limitless budget, pay for a vacation for someone. If you know someone who is always doing for others and never takes "me time," pay for them a room for a weekend. (Don't book it before you give it to them, unless you know their schedule backwards, forwards, and upside down. You wouldn't want to spend hundreds on a trip that can't be taken.) If you live near any hotel-casinos, and know your recipient will have no issue with the gambling, you can also provide a meal for them, perhaps a massage, room service, or gift card to an onsite store. If someone's idea of getting away from it all actually involves leaving everything behind, consider renting a cabin, or even a room in a b&b. If it's going to be in an area you're not that familiar with, be sure to research beforehand, and create a list of suggestions. Restaurants, historical sites, shops, theaters, museums, spas...base it on their interests, and schedule them a trip.

I hope you found this list helpful! It's not original information, but I think it's relevant and good info, and hopefully it gets your creative gifting juices flowing! Comment below your creative gift ideas!