Hmm. Dating advice from Norman Bates... What would Mother think?
I think he makes some good points -- the good shoes suggestion was very much on point.
I like Norman's idea of getting rejected a few times to ease your fear of being rejected. I just think you should choose a 'safer' (for your ego) situation than random women, who might be MUCH ruder than someone you are acquainted with. I'm glad to hear that you are getting some help for your anxiety problem - if that includes therapy, don't be surprised if your therapist sends you to get rejected!
If you have self-esteem problems (I guess that you did and that you were also young), then you should really ease into this. Overweight people don't necessarily have low self-esteem and poor body image, but I think this is what you meant by the "fatty mentality." As you can see for yourself right now, what you think about how you look is just as important as how you 'actually' look. Low self-esteem is not only often a big turnoff for women (unless you find a woman who likes a 'project.' But she often has low self-esteem, herself!!!), but it will lead you into BAAAAD relationships that will only bring your self-esteem down even more. Really, really start working on this before you get serious about meeting someone.
Where I must strongly disagree with Norman Bates is on the phone number thing. After some silly mistakes, I have learned to never consider a man who doesn't give me his phone number (not his cell, his work number or his pager). What is he trying to hide? I know MANY women who think the same way.
Give yourself some time. You've changed a LOT this year, and you're quite young.
I have some questions. How long were you overweight? Did you date or have a girlfriend while you were overweight?