Your room mate is a high class heir to a humongous heritage,
Honor in Japan is abouve all, so he has to be invested 100000000% in such a high quality babe.
You may be right in the hiding, Mc is simply mingling like any strong thug would,
like hitting on gurls in bars, like asking gurls out from the stores, like asking the personal trainer out.
Those are regular joe no standards antics, he does them as his phisique and looks certainly permit all.
Nah, just really wouldn't mess with hags in the first place.
The MC is was an elite assassin that faked his death to get away from his old life; I doubt he would be hitting anything and everything around him like a 13 year old. He would lay low and be more selective... maybe quality over quantity, which I'm not seeing a lot of so far in that city. The Doctor maybe?
Strange is the knowledge and the poise to follow through with the boss babe,
to go in the belly of the beast - the underbelly of high society, to hold his own with small time blackmailers,
guys wanting sexual favors for pics or what not. There he shines because such scum are his prey
when he was living the assassin life.