You get a security clearance based on what you'll admit to not what you've done. The basis of security is that some one cannot blackmail you for information based on knowledge of something that you wish to keep hidden. If you're ashamed of it I can use it to turn you into a source. If they (the man) already know what you've done no one can exploit your past misdeeds and you are not a security risk. It's that simple.

The only government exceptions are active duty military personnel who can't engage in certain sex practices and high visibility stuff (E.G. white house duty) where you may bring embarrassment to officials. I don't know what kind of jobs MessyONE is hiring for but it doesn't sound like the government that has to use fair hiring practices and is not allowed to ask certain questions. What type of bussiness is this? Who dictates the pass/fail criteria you speak of? What color, religion, and marriage status make you a pass or a fail? Every detail is scrutinized after all.