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I need more though. My main trouble on this will be finding some more good experiences (too much grief and shit in my earlier life, and too much of a spectator rather than a doer)
Well I'm sure there is a way to spin it in a nice way. Why did you change, what made you change. It's not bad to show some amount of vulnerability, as long as you show it in a angle that shows strenght of character as well. See were I'm going? Everybody has/had problems and rough times in their lives, especially true for people who have some amount of experience in life. Showing a bit of those will make you more human to her. Putting yourself on a pedestal isn't necesarly the way.
For exemple when I talk about playing guitar, I mention (among many other things) that one of my buddies showed me how to play because I was so crushed after a bad break-up I had years ago. It was one of the only things to bring me out of that mood... so I spin it in a way that shows that I'm not made of wood or plastic that makes me more human and girls can relate to this if they had any bad break-ups (which almost 100% of people had)