Why does your self-confidence depend on your looks? I used to have a toned body and thick hair, now I'm round and bald. And yet women approach me even, sometimes extremely beautiful ones, because I'm confident. I'm confident looks aren't that important to the kind of people I'm interested in, I'm confident that I'm friendly and kind, I'm confident that I'm intelligent and articulate. If you think the gym will fix your problems, then I propose you aren't tackling the root of the problem.I feel like one of the most self conscious people on the planet. I when I'm at home or in school I'm in sweatpants and comfortable clothes but before I go out somewhere I obsess about how I look. I workout 5 or 6 times a week to take out my sexual frustrations and to keep up the muscle tone. I also constantly post pics to get rated on bodybuilding.com. I am self aware and I think my maturity level is normal, but my self confidence is horrible and needs work.
As for the OP, if you want to ask her out, ask her out. I she says no, respect it. But be prepared for the fact that she fucks guys for a living. Sure, some SP's stop working when they have a bf, but most don't. If you're the kind of guy who'd demand she quit her job, consider she probably isn't for you because will likely just lead to resentment.