It is awkward, especially when you aren't sure how others are going to take it. Because American culture doesn't really condone talking about personal finances, you have a hard time gauging someone's reactions when the subject comes up, which causes a sort of opacity feedback loop.

I have a very good friend who just graduated law school and got his first job with some firm in Virginia. He helped me move cross country last summer, and got the job offer on the drive. On the drive, he mentioned his salary as a way of bragging (he likes to do that), and I casually mentioned that was a great salary for someone effectively right out of school. He asked what I made, and I told him it was in the ballpark of double his new offer, and that pissed him off. I had to remind him that I've been doing this professionally for five years, that I've got a strong track record of getting shit done and that I also have a grad degree in my field. It didn't really help, and it made things awkward for the remainder of the trip. I'm not sure why, though. We have another friend who makes far more than either of us ever will (he's some sort of associate director for a hedge fund), and although we don't know specifics it's fairly easy to come to grips with the fact that all of us make different amounts of money. I'm just not sure why the contrast between my attorney friend's salary and my own was such a shock, and it makes me very hesitant to discuss money with them in the future.