You're completely right about the "course on flirting and innuendo" - these used to come easily to me, but for a long time it's like that part of my brain had just gone dormant and now that I'm actively trying to use it again, the rust in the gears is making me feel even more socially uneasy. Plus, add the open/poly framework to that, and it's an even stranger conversation - "No, really, my wife is completely ok with this. We can call her if you like. In fact, she'll probably thank you." That's why my plan is to first seek the company of some other local polys, because it'll make at least some of that conversation less... weird. If that conversation happens, that is.
And I do know it's not a race, or a contest, and I'm not trying (consciously) to keep score. I only brought up sexual history as an example to show exactly how "in the hole" (no pun intended) my wife and I both are on actual experiences because of the fears people have of "tampering with us". And I also know in my brain meats that being a girl gives her a distinct advantage in most social scenes, especially conventions, but knowing that doesn't actually help things.
I did already ask M to drag me along on whatever adventures she has. Last time we went together (Penguicon, a linux/scifi convention in Detroit), she sort of... forgot about me... and wound up at a big hot tub party all night, while I sat alone in our hotel room. No, seriously. You're welcome to throw a "your friends suck" in here, I know, but they're the only ones I have.