Not to sound like a broken record but I again have to point out that, based the amount of time that has passed in the first 5 chapters and the number of planned chapters (16), this game should end around the Christmas after MC's first semester. It's a 3 month storyline without timejumps so the whole thing comes down to which of the LIs will MC consider to be his first girlfriend (since he doesn't consider Zoey to be such)
I still think there's the possibility of this story dragging out for a bit longer through a few time jumps. His life's been pretty chaotic these past couple of weeks, but ep 6 could maybe see him settle into something of a rhythm where the drama's all but non-existent for a while, and thus time-jump to a few days before his birthday in ep 7 or at the end of ep 6.
I also think that we could see something huge happen to the MC, probably caused by Quinn, that will see everything crumble around him and cause all or a few LIs to reject him, the DIKs and HOTs to reject him, and he becomes something of an outcast on campus. Then we'll fast-forward to the start of the next semester where the MC, after months of being a pariah, is now determined to make things right/clear his name, or whatever it is he has to do to get his friends and LIs back.