@Despairsometimes123
Sorry, but I think it’s a minefield.
Grieving in those circumstances doesn’t stop when his wife died, even though it may have been a blessing when she finally passed away.
If you were to date him regularly, what will you “say” to his friends and family and yours? I want to use the word “justify”, but that’s too strong, perhaps “explain”?
Do you want to be a bereavement counsellor?
I have a friend who went on holiday with a widower she met OLD. They went to his and his former wife’s holiday home in Spain, and although he insisted it would be fine he cracked up while there, and had a sort of breakdown, and she had to cut it short and fly him home.
I once went out with a married woman, met OLD, once. She was careful to first explain her husband had Alzheimers, and had suffered with it for some years, and she was setting up the next phase of her life. She told me she had already had another relationship outside her marriage, so although I wasn’t comfortable with it I did go out with her. But our second date didn’t happen as arranged -she called me to defer, because her husband had just died. She was a real mess, as is to be expected. I decided I didn’t want to take it any further, but never heard from her again anyway.
I subsequently had a long relationship (over 4 years) with a widow whose husband had died about 6 years before. She took great care to integrate me into her immediate family and big in-law family. She had prepared them all to the fact that she would be OLD. I consider myself very tolerant, but had to deal with the fact of her home being full of photos of her marriage and even being taken to her husband’s grave and being shown the empty space where she would be buried next to him.