My uncle, a musician, wants to buy me a guitar for Christmas. I'm really excited about this - I really really would love to have a guitar. And when he asked me what I liked, I gave him some general ideas, but stressed that while I wanted something that would sound good, I'm a relative beginner so I wanted something inexpensive, something I could upgrade in a few years if I wanted to.
He wanted me to go to a local guitar place and check out a few different shapes and styles to see what I liked the best. And suddenly, the gift became awkward.
When I gave him generics, I knew that I was still talking a pricey gift, but I could ignore the cost. Plus I figure he has all sorts of connections and could find something much cheaper than I could. But then I had to go to the store and see the price and then make a decision, knowing that he wants to get me something I want, but I needed to keep it in a reasonable price range.
I found one that seemed reasonable, but getting him the information just felt painfully awkward. "Hi, buy me this." Even though that's what he wanted me to do. Money and family is just awkward.