Losing the ego is so important for this stuff. On one hand, you sound like a fun-loving guy who likes people. Great. But you need to be able to transfer that over to dealing with women.
One time (circa 2006 AD) I was in Vegas. This HB6 was coming on to me rather aggressively, but she seemed cool, so ok. Her friend was a HB7, but cold as ice to me. She kept talking down to me. Eventually, the HB7 met some tall 6’2” Air Force dude. Before she left with him (and left me alone with my girl), she said, “Mike, you’re wicked cool. I’ve been such a bytch to you, but it hasn’t phased you one bit.”
The funny part was I honestly wasn’t “trying” to not GAF or have “frame” or any of that crap. I was genuinely having a fantastic time and kept smiling and laughing at everything.
See my point? A guy like you can easily be that way with much hotter women.
once I get the process rolling, I usually don't have a problem keeping it fun and pleasant
my 2 issues are
1)I hate risk and want everything to be super easy with no obstacles
2)I think that women have impossible standards and don't want to approach because I feel so hopeless