I don't think you can get 'out there' without some judgment. Let it be okay. Whose judgment are you not wanting to have? Random strangers? so what?
People you know? I don't think you're soliciting them as companions yes?
Dating doesn't truly change much over the years. In your fifties, you pretty much feel like an awkward teenager all over again. You just know a bit more and maybe are a little calmer, hopefully a little less rash. I regard that as part of the fun.
Be curious. Be fascinated. Want to know people. People respond to that. If you're thinking of the happiness and comfort of someone else, that's less thinking you need to do about yerself(yerselves).
Someone just had a link to a blog that I read and it was a lovely simple instruction for 'how to meet people' (particularly in a bar). Sorry, I can't recall.... but when you're reading her and someone recommends a blog, or has a blog in their sig, go look. If you don't have time to read right then, go back later.
Magazines are endlessly (tree-killing ENDlessly) full of advice on dating. All those things they say aren't different for poly ~ you just have one more required conversation (kinda like in high school, I wasn't 'required' to have the latex conversation, only the pregnancy conversation).