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Dear Blueman:
“I suffer from low self-esteem and a ton of insecurities“- this describes me when I was your age and many years after.
“I was unauthentic, trying excessively to be funny“- you didn’t believe that your true, authentic self was good enough for her, so you did your best to be someone else, someone worthy of her, someone funny.
You did it for her, because you cared for her.
“While being intimate once I said something to her that she didn’t like, which I thought would’ve been harmless“- you thought it’d be harmless. You didn’t have a harmful intent.
If you weren’t solely focused on your inadequacies, or imperfections, you would have noticed hers. No one is perfect. Everyone makes mistakes. Every day.
“I feel disgusted by myself how I handled the whole situation in most underconfident, foolish and anxious manner“- to me, you sound/ reads like a good, loving young person.
anita