I get the cycle now. Next chapter, he'll probably barely miss them as his depression drives him out of town with the dragons. He'll end up somewhere else, help/seduce another chick, get "dumped", and she'll join the ever-chasing harem. Wash, Rinse, Repeat.
It will culminate on him running into his childhood friend who originally "dumped" him and them reconciling causing him to give up on his dream of having a harem and devoting himself to his one original love. Finally the harem catches up.... I can't wait.