Disclosures of personal information should have a rational purpose. Say, if you were to move in with a woman, you would face the choice of presenting that woman to your mom as a roommate or as a lover. At that point it makes sense to weigh the pros and cons of being truthful, and, perhaps, lean in favor of presenting the woman as a lover to avoid possible awkwardness. Right now you are flirting with a manager at work; there is no rational purpose in disclosing random flirtations to your mom - you seem confident and you call yourself confident, so it is not as if you needed her approval or support. Then why disclose? What would be your purpose of and reason for disclosing?

I am asking these general questions because if you think along those lines, you'd be able to set internal policies and procedures that would guide you in your life as it unfolds, so that you can proceed consistently and systematically, which is better than dealing with each situation as if it had appeared out of the blue and you do not know what to do about it.