I feel like a total loser for being single and having no real romantic success since my long-term relationship ended. The deeper issue is that while I feel young and look young (people guess 20s), I am 37.

I'm an attractive, fit, educated woman surrounded by great friends, but the constant feeling of "losing" in dating overshadows it all. When I try, I either get:

  1. A 25-year-old who’s surprised I own a home.
  2. A much older man who wants me to travel on his retirement money.

It makes me feel like I’m failing at a basic life milestone. I'm afraid I'll never be mentally ready to date someone my age because they never seem to approach me.

Has anyone dealt with the deep shame or failure that comes from feeling like you're falling short of your dating goals, especially when you feel externally validated in every other area of life?

How did you shift your mindset from "I am failing" to "I am on my own amazing timeline"? I need to shake this feeling of being a "loser."


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