Flirting starts with not being attached to any outcome. You want to go into this with the mindset of having fun meeting someone new and interesting in the real world. And if it goes somewhere, great. If it doesn't, don't get discouraged. Instead, think of it as having had the opportunity to practice a new dating skill.
Growing up, we weren't taught who men really are and what makes them tick. I know I wasn't and in the past, I made huge mistakes that ended up emasculating men. It's what led me to helping women really understand who men are ... especially men over 50.