Hi there,

I'm a 28 year old male and I'm seeking some sense of guidance or advice with regards to my inability to let go of an old relationship from my past and a general consistent lack of success with women.

As a teenage boy, I dated a girl for a brief period of time that was my first love. As perhaps is not uncommon at the age, the relationship was rather unstable and additionally complicated by a love triangle situation as well as me trying to mourn and come to terms with my father's death which had occurred a few years prior. Unfortunately, after the relationship was over I started to develop symptoms of chronic depression which to this day I struggle with mightily. It took me several years to really get over the relationship. However I eventually started to date other women and went off to college etc. I recall at one point looking back at this old relationship and not quite even remembering this girl's face. My feelings were relatively neutral and most if not all of the toxicity was gone.

Fast forward to today, I have been single now for 8 to 9 years and seem to have rekindled the same type of toxic and obsessive feelings that I had in the wake of that old relationship as a teen. I made the huge mistake in the past year of getting reacquainted with this girl on social media and have developed a kind of masochistic habit of looking at her Instagram etc. This seems to have re-triggered my old tumultuous feelings and I am constantly bombarded by thoughts of this girl throughout my day. I catch myself in the act of fantasizing about her on a regular basis and seem to do so almost like a reflex, effortlessly. It's as if the relationship had an almost traumatic effect on my psyche, and yet there is something comforting and pleasurable about returning to it in my mind even though it's damaging. Fortunately, I've been able to force myself to stop looking her up on social media and am currently in therapy, just started a daily meditation practice, and just started taking Prozac as well. I am hopeful that with some time and effort things will improve but it is truly a maddening experience to feel like you are powerless over your own mind.

What has made matters worse is that since I have been single for such a long time I haven't had any real life outlet to develop healthy new relationships with women to perhaps replace this old toxic one. I have met with an enormous amount of rejection the past 8 years despite taking chances and putting myself out there. Compared to the peers of my age I have very little relationship experience or sexual experience. This has left me feeling dejected and like less of a man. Ironically, 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. Perhaps if I could achieve that happiness and emotional independence, it would could also help me let go of my old relationship and the lingering pain there as well.

I apologize for being so long-winded here; I just wanted to describe my situation as accurately as possible. I'm trying the aforementioned meditation/medication stuff in therapy and am hopeful but any thoughts, ideas, or resources with regards to these two issues would be helpful. Thank you!