I think this all stems from the fact that K and Retro have two completely different goals in mind here , no one is actually wrong !

K is out to have fun , be challanged and meet women

Retro is out with the pure purpose of finding 'the one' and having a real relationship

If K is out to have fun , be challanged and meet women , why wouldn't he go to fun places where maybe the girls will put up a challange and he'll have the pleasure of convincing her how awsome he is !

If Retro is out to find the one , and wants to do it with as little resistance as possible , why wouldn't he go to places where he has more time and less pressure of being blown out .

Two completely different ideologies , both correct in respect of the end goals