Dear Kale77,
I'm sorry life has thrown you so many curve balls. You can be proud about the fight you have waged and still are waging. I'm in my 50s, so dating may have changed but before I met my spouse, I was quite open about dating a variety of people. I found it attractive when a man shared my interests. I liked to be "taken out" but was not at all impressed by how much was spent. In fact, I once thought that someone was a bit foolish when they spent over $100.00 on a dinner for two (expensive restaurant). My favorite dates: a truly awesome hike, it wound through caves where water dripped (it was in the southwest were the moisture was refreshing and uncommon); the boy just brought some water and very light snacks in a small backpack. With my husband, camping on top of a mountain, under the stars. He brought a tent, hotdogs/buns, and beer. I also appreciated $1.00 movies (do they exist anymore?) and eating pizza by the slice while sharing a pitcher of beer.
From my perspective, don't be afraid to ask someone out. The worst they can do is say no. If you don't hit it off, then you'll only have to endure one date; but I think attraction can be very hard to predict. I liked men who had admirable qualities but for me that would include intelligence, humor, enthusiasm (about something that strikes me as interesting), and bravery. Hope these suggestions might be helpful.
Sincerely, Myst