so i am new to the whole scene and i have a guy mentoring me but he never answer one question that irks the bejesus out of me. I've noticed that it is harder for me to approach targets that met me during my down and out period, it seems like they can't get over the old me. are there any pointers or guidance i can use to start the game over again?

I can relate and while not impossible, it is intricate. I believe women unconsciously make full judgment within the first couple minutes of contact, which is a semi solid image that seems hard to change once drawn.
Healthy distance, true self confidence and happiness is the only way to regain some to most control of that image.

True . . . but women are also insecure. You ever go shopping with one? Holy crap!

Man: "Yes, the blue one is prettier, go with the blue one!"

Woman: "Are you sure? Because I think the red one matches my shoes."

Man: "OK, go with the red, the red is nice!"

Woman: "But the blue one is _____."

So if she has a certain opinion of you, all she needs is a little stimulus to re-educate her. You need to go sarge up a fresh fun girl. Then once you have her rapport, you need to parade her around your old grounds just once to get the ol' gals' re-processing their opinions of you.

I wish my old "friends" were even half as hot lol