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Gifts For People You Aren't That Close To
The pithy 21st century television scholar Dr. Sheldon Cooper, from "The Big Bang Theory," said this about gift giving:

"The entire institution of gift giving makes no sense. Let's say that I go out and I spend 50 dollars on you. It's a laborious activity because I have to imagine what you need, where as you know what you need. Now I could simplify things, just give you the 50 dollars directly and you could give me 50 dollars on my birthday, and so on, until one of us dies, leaving the other one old and 50 dollars richer. And I ask, is it worth it?"

What he is describing is what many of us feel like when we are buying gifts for the "not-so-personal" people in our lives. These are people either that have done something for us, or with whom we have a relationship but just not people who hold a place in our heart.

Mail Carrier
If you know your mail carrier and thank him or her for his or her service, that is more than he receives from most people. If you want to give a gift, keep in mind that you are not allowed to give cash or a check to a postal service employee. You can give a gift, provided it is below $20 in value. A couple of appropriate items may include a gift card to a coffee shop or a warm pair of gloves, especially if you live in a place where winters are cold.

Your Boss
One survey found that 48% of respondents (nearly half) said they don't give workplace gifts, so you may be off the hook when it comes to your boss. If you are required to give something, then first consider a group gift. It will likely be cheaper and keep others in the office from comparing your gift to other gifts. If you want to do something personal, homemade cookies or a modest gift card is always appropriate.

Just Started Dating in December
First, try not to start a lasting relationship in December, but it's probably too late for that now. You are in an awkward spot in which the gift isn't as important as the message it sends. Too extravagant or personal and you end up sending a "where should we have the wedding?" message. If it's not thoughtful enough, your message suddenly becomes: "What did you say your name was, again?"

The answer is obviously not cut-and-dried, but early in a relationship it is best not to use the holiday season as a time to send any message. Keep your budget low, about $20 to $50, and concentrate on something you know he or she likes. Maybe a book was mentioned, or a certain food or brand of coffee. The most important thing is to avoid sending out a dismissive message by under spending or an aggressive one by spending too much.

First Time Meeting the Parents
Nothing says "awkward" like meeting your new love interest's parents. Pins and needles don't even begin to describe it, and if it's the holidays, you had better show up with something. Once again, the key is to stay muted (in more ways than just the gift) and not try to over-impress. A bottle of wine, candy or an offer to bring something for the holiday dinner is likely enough. Getting dad a sports jersey or mom a small appliance is asking for trouble.

Co-Worker
You spend a lot of time with these people and often more time than with your family. The problem is that within this circle lies a virtual potpourri of acquaintances - everybody from dear friend to frenemy to "that guy you really don't like much." What do you do about this gift-buying conundrum? The answer is that you forget about overanalyzing the relationship. Everybody gets the same thing, and if dear friend deserves something nicer give it to him or her later. Alternatively, instead of gifts, suggest pooling money and going out for a team dinner. Even better, suggest donating to a local charity or helping somebody in the office who is having a rough time this year.

The Bottom Line
An awkward gift-giving situation is one in which the size or nature of the gift isn't obvious. Each situation is different in its own way. Nevertheless, all share one trait: The need to fine-tune the gift so that it doesn't misrepresent the relationship.

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