An awkward situation
So I'm starting to develop feelings for someone who's been in my life for a while. My status as a poly person is widely known in my group of friends, though I haven't been that successful at it.
I have a couple issues that complicate the situation. First, and most complicated, she's a widow. It's been a couple years, and I thought she was getting better, but the last time I talked to her I found out she's still heavily involved in widow support groups, which makes me worry that my stepping in in any capacity other than friend would risk hurting her in some way.
Second, I, generally, suck at telling if someone's interested in me. Coming from a bad self esteem (bullied growing up), It's always hard to tell which direction to go. I know my instinct is to hold back, be patient, and not risk upsetting things, because that's what I ALWAYS do. Unfortunately I also know from experience that this cautious behavior allows many things I wanted to pass me by.
So. Is my instinct correct, and patience, continued friendship, and trying to get past her walls is the best way to go, or am I risking losing something by holding off.