Filling in gaps.

I've recently gotten addicted to the site Gumtree, which is an Australian site that you can sell unwanted or secondhand goods for. There's a story to be told with so many of the items there, though it might just be my imagination. So many wedding dresses sold to be rid of because they're "never worn." An engagement ring valued at 3000 being sold for 2250 ONO, because the seller "really just wants to get rid of it now!" I fill in the gaps of stories I don't know.
I recently had a trial shift waitressing at a restaurant. My shift was on Saturday, and an elderly man came in, and sat at a table alone, finished his meal, paid, then left. Apparently he's a regular, who comes in every Saturday night and eats the same meal at the same table with the same lack of other people. I feel sorry for him, but in doing so I feel intrusive. Do I have a right to? Maybe he does it to remember his wife, or because he wants to go out without anyone to go out with, or enjoys the restaurant and likes to treat himself... I don't know, I have no right to judge, though what I'm doing isn't judging. My gap filling mind doesn't leave room to the imagination. Sometimes when I'm sitting on a bus or a bench and can see two people conversing I'll make up what they're saying to each other. Once this led to me feeling incredibly guilty, because in my imagination I'd made a boy and a girl break up with each other. The girl half walked, half ran away crying, and the boy sat at the table with his face in his hands. There's no reason I should feel guilty, I don't dictate others lives through imagination, through filling in the gaps. Nonetheless, I do feel guilt and shame.
I become far too emotionally invested in things which should not concern me. But this doesn't really bother me.