I hope my reply helps. You wrote:

"I seem to get along fairly well with women on a friendly and conversational level, but seem to lack the ability to attract the people that I desire. I do not consider myself entitled to a woman's affections, but naturally after so many years of rejection, it is difficult to not feel deeply hurt.

My lurking suspicion is that my long time struggle with depression has been the major culprit with regards to my lack of success with women and that I have come across as too emotionally vulnerable or needy. Part of me thinks that I should to the best of my ability drop thinking about women/sex entirely and focus on other areas of my life until I have rebuilt a healthy sense self esteem independent of those things. It's so tempting to think of myself as less of a man and a person because I'm not good with women."

You've shown some insight here and what I have quoted is what you can discuss with your therapist. I would try to find a male therapist, by the way, particularly because you have issues with the concept of manhood and manliness. Group therapy might also be helpful.

I might point out, too, that for a healthy relationship (and not one that is solely based on "desire") having this ability: "I seem to get along fairly well with women on a friendly and conversational level" is invaluable, since 'getting along ... on a friendly and conversational level' is a wonderful quality that will last your whole life, long after you stop being a young and virile stud.

In my opinion, our 'selfie society' where snapshots of airbrushed faces and pneumatically enhanced breasts and buttocks are everything has left people with no knowledge of what a real relationship is. Meditation and medication are fine; but so is getting outside of yourself -- do you do any volunteer work? Volunteering alongside women who are also outside of themselves might be just the ticket to help you see what is really important in human relationships.