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I've never had a girlfriend because I'm to awkward to just ask out whoever I'm interested in, mostly out of fear that it'd damage whatever pre-existing relationship I have with them. And I'm too shy to talk to women I don't know.
The one time I actually did ask someone out it was right at the end of high school and she said yes, but nothing ever came of it, probably because I came on way too strong with trying to follow up.