I want him to know what the AI did, I think it should be standard requirement to report on anything out of ordinary for instances like this where if he had a conversation with the someone the AI would replay it
ThanatosGreekGod:MC was training in VR, some girl walked up and asked him out on a date, The AI took her out then awnsered a bunch of questions letting it be known he has 3 wives (Currently in Bleach world) and this knowlege would undoubtedly spread due to gossip unless you author forget/decide against that as a little plot point