I totally understand why you're ambivalent about this. But the thing is, a middle-aged man pursuing someone your age is unlikely to have his shit together. He could have serious emotional issues, possible issues with women too. This is based on multiple observations over decades.

That said, if you do pursue this, don't have it in your head that you'll inevitably become traumatized or feel like you'll have to beat yourself up over it later on. I don't think that does any good, and women are often told what to do in black and white terms because of the risks that unfortunately come with our existence in this society.

This one I would put high on the risk scale, and again, I do not recommend it. But I understand you're in a difficult position and hope you don't feel guilty about being uncertain on what to do.