Slightly modified, the notion could make for a convenient way to ask a female friend out. It allows her the opportunity to ignore it without being rude.
I have a similar issue with your chancemail idea. I can just about see the 'let fate decide' value, and also the bit where the receiver gets to pretend it never happened if they wish. But the bit about paying to remove all of this, and add in the receiver's mind the suspicion that you probably did so really muddies the waters.