Simple, I don't. I ski whenever and wherever. It doesn't really matter to me as long as I get to ski.
My best friend and I ride together 95 percent of the time. Usually one of us drives and the other buys food after. We switch that up a bit and that's how we plan that out.
If you're having trouble with planning rides, start a group chat with the guys you're gonna ski with. That way you all are on the same page with what's going on and stuff.