I love to give gifts and I am often given credit as being a great gift giver so I thought I would share my thoughts on giving gifts. I realize this would have been a more useful post a few days/weeks ago, but the inspiration didn't hit me until last night.
It's the thought that counts. That being said, it's important to remember, it's the thought that counts.
DO NOT give... a vegetarian a gift certificate to a steakhouse, a recovering alcoholic a membership in a beer/wine of the month club, a paraplegic tap dancing shoes, a deaf person an ipod, or a blind person a new TV. This kind of gifting falls into the category of "thoughtless" and will undoubtedly hurt feelings. Some of these examples might seem extreme, but there's tons of lesser examples that fall into this category as well.
DO NOT give a gift that implies a not-so-subtle HINT unless you know damn well it is consistent with what they actually want. e.g. don't give a smoker nicotine patches unless they've said they are actively trying to quit, don't give a woman a membership in a weight loss meal club unless they've said they wanted that, a balding man a hair club membership unless they've said that they wanted that, etc. While you might think you have their best interests in mind, it's insensitive, shitty, and passive aggressive. You are projecting what you think they'd want when in actuality you are hurting their feelings.
It's the thought that counts is hard to adhere to unless you think about what the implied thought actually is. This thought shouldn't be what you think they should be, but an understanding of who they are and what they like.
As you get older people are less likely to say "I want X or Y," and this is why it's often easier to shop for children. Giving a good gift is easy even though it might seem difficult. The more time you spend with someone the easier it is to find the perfect specific gift. For people you see infrequently (such as extended family) your gift will rarely be perfect, but it can be very good by simply exercising your existing knowledge of their interests and translating that to gift form.
Distant in-law #1 you know loves to micro-brew. You have no idea about micro-brewing. A gift certificate to an online store specializing in micro-brewing supplies and ingredients will be superior to a gift certificate to Kohls.
In-law #2 has a serious collection of art-house films on DVD/Blu-Ray. You have no idea what they have and don't have. A gift certificate to a store that stocks Criterion collection movies (such as Barnes & Noble or an online store), to a local theater that specializes in independent and foreign films, or even a Netflix subscription (if they already have one it will just stack on their current subscription and save them money) should go over better than getting them something completely unrelated or taking a stab in the dark on a movie they may already own or didn't like.
When all else fails, you can always ask.
For people you see more frequently this can be a lot easier since you have a regular glimpse into their day to day life. A good gift for them splits into three categories:
1. Something you know they want (and/or related items).
2. Something you know they need but haven't purchased for themselves.
3. Something that shows that you know them and what they like.
#3 is basically the same as my previous examples.
#2 probably won't seem as appreciated right off the bat but you will likely get repeated thank you's down the line. e.g. if you know they eat a lot of rice but generally boil it on the stove, a rice cooker is an easy gift that just about everyone can use and appreciate. If you share rides and know their windshield wipers suck, drop for a pair of top of the line Bosch Icon wipers (make sure you get the year/model of their car before doing this).
#1 is easy since it's already been known. If you plan to get them more than you know they already want or you know someone is already getting them the "big" one, build off of that idea. If she wanted a specific coat, in addition to the coat go after a matching hat, scarf, and gloves that are consistent with her style. If he wanted a Dewalt Cordless drill, an extra battery and charging station always comes in handy. These serve as a great complimentary gift and will make them think of you each time they use the item, even if you weren't the one that bought the big one.
Re-gifting a bad gift or gifting something you got for free only works if the item is perfect for someone else or you really don't care what they think of you.
Remember that it's the thought that counts... but it's the thought that counts. I received a bottle of booze from my relatives for the fourth consecutive year this year when I haven't had a drink in over 10 years and haven't had more than 1 drink in a sitting in over 15 years... and earlier this year I even told them that I don't drink at all when they wondered why I wasn't having wine with dinner. At least booze can usually be re-gifted without hurting anyone's feelings but my own.
If you are a sub buying a gift for your Mistress, it's usually not recommended to buy any BDSM gear unless she picked something out that she specifically wanted. Submissive fantasies often skew the gifting process if you choose one on your own.