I imagine it would depend on whether he's doing that sort of stuff in front of the girl he was dating at the time or not.
We obviously don't get the full picture and only his (possibly biased/unreliable) interpretation of his behavior in the past. But, call me crazy, I'd probably be a little miffed if I was hanging out with my boyfriend and he was praising the looks over others girls or going off to help them out, in the exact same manner he did with me, and I was there in front of him while he did it.
To me it sounds like the ML never learned the nuances of relationships and the ins and outs of the hierarchy of importance that people can have in one's life relative to their 'relationship position'. Maybe (likely) that's a result of his being raised in an orphanage, without stable & long-term parental figures and children his age with whom he could build actual friendships.
If that's the case, then he's a sympathetic figure in that regard, but however well it worked out for him in his "normal world", the rules are very different where he is now, and that same sort of behavior might prove detrimental if not outright dangerous where women latch on much more readily to any man who shows kindness & consideration, but have not "other options" to go to if they face competition for that man's attention from other women, and thus might be more assertive/aggressive in "staking their claim", whether toward other women, or the ML himself.
In that sense, it's in his best interest to unlearn that behavior before it starts causing him real problems that he's remained relatively unaware of due to the circumstances of not running into multiple other characters simultaneously in any considerable degree.
