In one way this is horrible, in another he stopped being their playball. Well, he could just have turned his heart into stone in a different way, pick one and break the hearts of the others. Preferable the tomboy or the play-pretend-littlesis girl. The other one is too tsun and the last one just friendzoned herself/doesn't count anymore.
But as he seemed to be too softhearted for that and isn't ready to leave behind his current way of thinking about how a romance should look (I don't say he should. It's all his choice.), he might have taken the right route. Surly a rather expensive one, as he discarded some beautiful girls, he has some good connetions to and memories with, but if he really can move on and is willing to hit on a different girl to actually get somewhere, his choice might actually have not been that bad. IF he manages to get a GF, that is.