alright so if i remember correctly, you'll come across three options while out on a run, it's after meeting (or avoiding) the man crouched down at the side walk, and it'll reflect on whether or not you feel guilty over the hit-and-run done by the apartment complex across from you.
you have to choose the first option; if you choose the bottom two, i'm guessing it'll pretty much lock you out of any attempt of caring/getting to know the other characters since you're determined on you goal, finding lawrence. in this case, most especially, you'll keep hitting that dead end with wingdings
kept dying to wingdings too a while back and this seemed to work while i was trying to find a way to avoid it. hope this helps :D