“Being yourself” does not preclude personal development. It’s not in our best interest to be the same forever. Personal growth and learning new skills, even something like flirting, is part of becoming a more well-rounded version of yourself.

Thing is, flirting isn’t something you need to master or even be great at. As a matter of fact, being “terrible” at flirting can be just as effective.

The goal of flirting is to engage in social interaction that expresses interest and attraction.

You aren’t trying to change your personality, but rather get better at communicating. “Flirting” builds rapport, gauges interest, and creates emotional or romantic connections. It can be a fun and lighthearted way to engage with others, but that isn’t the point.

Honestly, I think you’re putting too much pressure on yourself with all the thought you’re giving it. You probably shouldn’t even call it flirting. Put that notion aside. Focus on intentionally communicating your interest.

If you’re interested in a person, then find ways to express that. It can be light-hearted and flirtatious, but like I said, being terrible at flirting works too. So do it terribly. You’ll eventually figure out what doesn’t help communicate your intent. Flirting is a gentle and indirect way of expressing that intent. Many people are simply more direct and it works for them. That may be better for you as well.

Regardless of what you do, be respectful. Be playful if you want. But most importantly, communicate your intent and desire.