How does a lonely 55 year old male find the right woman?

I haven't been in an intimate relationship since the '80s, and I haven't asked a woman out since I was in my late thirties - I decided to stop trying as a means of self-preservation when I realized that I take rejection worse than most people. My hope was that if a relationship was going to happen, it would happen naturally, but it never has. I've been on a handful of really bad blind dates (my friends for some reason only try to set me up with overweight women, which I'm not attracted to) and dating sites and apps have not worked out for me. I'm only average in the looks department, but I'm physically above average (5'10" 175 lbs and work out most days). I'm in a position to retire and buy some land in the country, but I can't see myself doing so without a significant other by my side. I'm curious to read your thoughts and advice.



Submitted December 20, 2019 at 11:56PM

I haven't been in an intimate relationship since the '80s, and I haven't asked a woman out since I was in my late thirties - I decided to stop trying as a means of self-preservation when I realized that I take rejection worse than most people. My hope was that if a relationship was going to happen, it would happen naturally, but it never has. I've been on a handful of really bad blind dates (my friends for some reason only try to set me up with overweight women, which I'm not attracted to) and dating sites and apps have not worked out for me. I'm only average in the looks department, but I'm physically above average (5'10" 175 lbs and work out most days). I'm in a position to retire and buy some land in the country, but I can't see myself doing so without a significant other by my side. I'm curious to read your thoughts and advice.
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