Being known as the person that always carries a camera with them is a lot like dancing. You either acquire the skills and become comfortable with it or you spend your entire life agonizing over how people stare at you comically because of the lack of confidence you may have doing both.
I decided early on that I prefer being confident at the expense of being pegged as the guy that everyone can count on to have a camera for any occasion. I generally put out a call to most friends in the area and ask if they would be up for the adventure of exploring taking a few portraits while exploring places in which they wouldn't go out of their way to visit on their own anyway.
I acquire more confidence, improve on my technique, learn to direct people as far as posing and they get the high of reclining back on their chair in front of their computer and keep tabs of how many Likes they gain from the photos I took and they uploaded.
Diana is not necessarily this type of person but she certainly had the required patience to put up with me as far as venturing out to specific locations so that I could get the shots I envisioned based on our surrounding.