I've always been careful and cautious and refused to take risks but I want to get out of that habit and always make the bold move. However, I'm not sure how much I should care about the repercussions or if I should always think things through. What is your personal mindset when you do bold things?

SOMEWHAT RELATED - OPINIONS WANTED: I also have a specific example that I'm considering but I'm unsure of how things would turn out and would appreciate some advice. I have a "plate" (mostly just a girl I've fucked at/after parties) that is definitely interesting and has me actively trying to get with her more than most women. However, she has been playing hard to get lately and trying to bring me into her frame, while her closest friend has been coming on to me and giving a ton of IOI's recently.

Both girls think my n-count is a ton higher than it actually is and see me as a player that could possibly be tied down. Since that is the persona I'm giving off, would going for it with the friend and actively trying to game her more than casual flirting make them work harder for me or would that end with it blowing up in my face with both of them?