I just wanted to put in my general thoughts about some of the loose ends that people are commenting about. I do agree that there appear to be quite a few loose ends ... and while while there's nothing wrong with a game leaving you with questions, I don't think some of them are as loose as they appear. There's no definitive answers, but there are definitely clues.
I'll be honest, the one thing that I had to "set aside" after playing the game a few too many times was the timing.
It's been 10 years since the beginning of High School, you were with Steph for almost 3 years, she left you the night of the prom, but you didn't get the money until after turning 17 and it's only been two years since she left you. I don't have THAT much of an issue setting all that aside, because the overall story is that moving to me, but even now I have to tell myself to let it go at least once per play-through.
I agree with the relative/grandfather vibe, the question is what does this character and this scene contribute to the story. What would be lost if that scene didn't happen? In my opinion nothing. Same with other secondary plotlines (the bully, the sister etc)
The story's main strength is the characters and the central idea of overcoming emotional difficulties by letting people into your life and changing your course and theirs through friendship, emotional connection, love, sex.
Too many secondary plot threads, especially if they lead to a hasty or no resolution, overcomplicate the story, without a need for it.
Same with the LIs. Too many in my opinion, which gives this nice harem vibe, but aiming at the same time to have some measure of realism, so you have to choose. This results in some girls feeling like they would be better as friends/fuckbuddys and not full-blown LIs, at least for me.
So for me the main LIs are 3:
-Steph. The ex-girlfriend, the great love lost for reasons outside of either's control, misunderstandings, mistakes. She comes back, explanations are given (even outlandish ones) and the relationship resumes. Fairly realistic, good feelings, I'm sold.
-Lexi. The fantasy, the discovery of the real person behind the celebrity, the princess and the peasant trope. A little soapy, but it works for me, it's entertaining.
-Cece, of course. The charismatic yet very troubled new person, the emotion and connection that change each other's lives. The central plot of the story. The "canon" girl if you will.
The other girls for me work way better as friends than LIs.
-Kira/Robin. The first girls the MC meets, he opens up, they have a good time, some sexy times, they help each other with their issues, and form a great friendship. This works way better for me than the throuple.
-Linda. The childhood friend/first crush. They reconnect, have some great fun, sex and conversations and help each other move on as friends. Way better for me than a couple.
-Holly. As hot as she is, she seems like an afterthought, as others have said. The temptation in Lexi's path, a porn-logic opportunity for a threesome or for Lexi not to be alone if she is not chosen. Works only as a friend(a very hot friend) for me.
Any way, sorry for the long post, just my 2 cents on this very enjoyable story.