I never really understood this, if anyone asks "are you a virgin" and the answer is outside the scope of "yes", the answer is no and anyone seriously considering marriage can put that together. Virgins are proud of their choices, and they made the choices so that they could say "yes" in that conversation with a marriage prospect. Unless the hope with this message is for virgins to start shutting down the question, which would be unlikely.
Why play a stupid game like that with stupid humans? If you made your repentance to Allah SWT , stand on business and be honest about your dirt. otherwise it's betting against time, a bet that your past won't come about any point in your future. What's for you is for you, and what isn't, isn't. Lying by omission and obfuscating aren't a solution, and inquirers aren't going to feel shame for asking a tough but important question
My reasoning applies for the situation at hand, where the inquirer obviously isn't adhering to the principle since they're asking. Now the person answering the question should respond with the principle in mind, but if the only people saying "don't ask about it" are non-virgins, the outcome is the same, the inquirer got the info they needed, just not in a "yes" or "no" fashion
I know it's an islamic concept to not engage in publicizing sins. Does it occur to you that responding in the way the sheik recommends, could still be seen as disclosing sins? Today there may be an argument that it's not, since it's not explicitly stated, but the way language is used changes generation to generation. In 100 yrs, it could be common knowledge that "Allah said don't ask about this!" Is something stated only by non-virgins. Islam doesn't change, but the people and societies do, and this creates nuances. Burying your head in the sand and thinking "I am the Muslim following islam the right way, the other Muslims arent" isn't special / insightful