I've never dated much and I've been insecure about women most of my life. Twi years after my marriage ended I've been worse than ever. It seems that to get over my insecurity I would need to get out there and meet women. But emotionally healthy women don't like guys who are insecure. Am I doomed to be caught in this Catch-22, so there's no point?
You know something? If you aren't confident, just 'pretend' to be confident! This may sound like bad advice, but it isn't.
People always advice us to 'get confidence', but they don't understand that it can't just be 'got' like that. But pretending to be confident is not hard at all. And eventually, this 'fake' confidence will turn into real confidence.
Trust me, it works! So your situation isn't even half as hopeless as you think. Just go out, meet women, talk to them with your 'fake' confidence, and you'll likely taste success sooner than you think! :)