@AbuHajaar
It is not as much winging it as it is looking for opportune moments to do pre-planned skits. MC has a long list of scenarios he wants to play out. So he looks constantly for moments when he can. If none appear, he tries to make one himself while not being too obvious about it. Granted, some of the details are just what he came up with on the spot, but all of his ideas are based upon a planed-out, core idea.
Shadow Garden almost only works using heavily planned and finly tuned actions. Almost none of it is left to chance because the girls are way to caught up with not being a burden to, becomming as useful as possible to, and/or becomming a potential future love interest to MC (though the love interest part is more of a side goal which almost if not all of them share, which makes them slightly possessive of MC when dealing with girls outside of the main leader group).