I spend about 2 years preparing for the right moment, I talk

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I spend about 2 years preparing for the right moment, I talk to a lot of girls to get the hang of talking to her, I spend countless hours preparing for the worse scenario of rejection, even date a girl for a little bit as friends to get the feel of being around a girl in public and the I see social media crying about a car accident. "Who is it this time" I say with a small smirk on my face before I read the word Ashton Hunter. My whole world falls apart and I go into a small state of depression before one of my friends notices how sad I was when even me myself didn't realize how crippling this is to me. I need some help getting over this, any one who has had any similar incidents and got over it please share.