Dating
11 h

Early thirties and I’ve never dated. What should I do?

My situation is a bit different than most 30-somethings that haven’t dated. I haven’t been on a 15 year rejection streak. I gave up on dating at different points of my life, like when I was in the military (super limited and competitive dating pool), and during financial or family hardship. The last time I got a yes was senior year, high school. She played games and didn’t want to actually date me, and I learned about compatibility from that experience. She said yes going on a date but no to all my plans while also making up other dudes being interested in her. I withdrew my invitation. The last time I asked someone out was when I was 21 and in the military, and she said no, and said it was because I’m mixed race. Something that’s been on my mind is a blunt memory from a different girl I tried to date in HS. She told me that I was sweet and kind, and that were good traits to have. But she said that I was not brave enough and let people walk all over me. She also said that she felt like held myself back too much and stuck to safe conversations. That was a long time ago, but I think what she said back then still applies right now. I don’t want to think of myself as undateable, but I can’t summon the willpower to try anything. Cold approach doesn’t fit my personality. Dating apps seem like an exercise in frustration for a lot of people. I can’t picture myself going to a bar. I need to do something different but I can’t decide what.

Early thirties and I’ve never dated. What should I do?
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