Thanks, @Bill3, much appreciated. I've been thinking over why I tend to end up in these spots, they all feel so similar. Initial attraction (either way or mutual), then a honeymoon period (could be anywhere from mere days to over a year), then I start saying or doing things that make her pull away, then I get needy and desperate. Usually the woman blocks me first, but in this case I just felt so much pain and hopelessness in the face of her romantic rejection of me.

Part of the healing agent part that you suggest, I think, is approval seeking. Don't get me wrong - what makes this time so much more painful than before are the ways in which she and I actually have great compatibility and hit it off with great chemistry. But from the moment that I started to reveal things I am insecure or worried about, I was not able to hold it together about worrying over losing her approval. And of course part of it is to be expected anyway. For better or worse, I could not control if she felt a progressive loss of respect for me for not only hiding my money situation from her, but also whatever thoughts about the future she now saw were delayed or no longer possible with me. That downward spiral led me to send her texts of stuff I was doing to improve, which is all well and good, but as others have said it just made me see her as more of the way to fill the gap in my life when I saw the writing on the wall that she had pulled away.

Drinking for sure has been the common denominator is almost all of my post-divorce issues. I mean, I hadn't realized I was probably medicating with it since freshman year of college, but since my divorce these gut-wrenching breakups have made me feel even guiltier about drinking because it leads me to impulsive and off-putting behavior. It it rough, and most days I don't have hope of beating it. But I guess I have to try.