Holiday gift confusion

With the holidays upon us, it is no surprise that I have wondered who it is appropriate to buy a gift for.  Of course I have my usual: parents, grandmother, 2 aunts, nieces & nephews, 1 work gift, and 1 cousin gift, but what about the few extra people that you think about this time of year.

I have this fantastic co-worker and we have become good friends this year.  Buying her a gift seems like a really nice thing to do, but I don't want her to feel obligated or continue down a gift path.  I'll probably give it to her anyway because I know she will appreciate and use it.  Maybe I won't wrap it and give it to her in January just because.

What about someone you just started dating?  You don't know very much about the person although you have some great ideas but if you started dating at any other time of the year you would not get them a gift so quickly, it is just bad timing.  Should you be prepared just in case?  How much money should you spend?  Can it be something homemade or simple - like a knitted scarf - or something they casually mentioned one night even if it is over $150? 

Then there is always the tips for the mail person and garbage men but what about the other service people?  I don't get a ton of packages and I couldn't tell you who my FedEx/UPS person is.  What about the aesthetician that are removing my hair - am I supposed to give them a little extra or go out of my way to see them before my next appointment?  I bake cookies for my building concierges and my coworkers, but is that enough?  What about my clients - aside from sending them a holiday card, am I supposed to do more?

Of course there is always the people you completely forget about.

And what happens when you receive a gift from someone unexpected, and you are not prepared? Or worse, what if someone gives you this amazing gift and you only spent $20.

I try to put a lot of thought into my gifts these days, and I get a great deal of joy from someone who actually likes their gift. I try not to get gift cards unless I am completely lost on an idea.