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How to date after 14 years single?

Anonymous
Feels pretty pathetic to ask but yeah I've been single so long I dont know how to date. I dont even know how to begin a relationship. Online dating hasn't worked for me, not for lack of trying or interest. A few messages have been sent but not so much as a single meetup. A couple of people have seemed to express interest in me over the years but i haven't been able to return the affections in a way that i felt was fair so they never went anywhere. I expressed interest in a couple girls over the years that turned me down flat and in those cases it wasn't until I had spent significant time around them that I developed feelings or romantic interest.

I know there are a lot of assumed skills or experiences that I would/should be expected to have that I am lacking. That inadequacy makes me withdraw further from attempting to approach anyone I might be interested in though. How would you suggest going about breaking out of this state?
How to date after 14 years single?
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