OP - I know exactly what you mean about feeling awkward about your friend telling you how they are practically drowning in debt but still talk about their upcoming trip, new this, new that, etc. I've been there, and I know how mind-boggling it can be (to me, at least).
While I can't tell you what you should do, as each person and relationship is different, I can tell you what Dh and I did. When we realized that if we wanted to get ahead, we needed to stop living on the next paycheck. We needed to live in the NOW. We began living within our means and paying down our debt. We paid cash for everything. We were pretty open with our close friends about what we were doing. Many of them scoffed and told us we were dumb, that's what credit was for. Whenever we got together, they encouraged us to spend, spend, spend, "just put it on the plastic!" As time went on, Dh and I didn't look forward to going out or even getting together with them, as they just didn't value the same things that we did. It's like we were ready to grow up, and they weren't. Over time, we lost touch with them (long story there).
Maybe I am judgey, but I choose to spend my time with mature, responsible people, who contribute to society. I understand that at times, people get down on their luck, because believe me, I've been there too, but I feel that financial decisions that you make for yourself/financial priorities say alot about who you are.