I really like the game and have enjoyed it so far. I have reached the end of content for two branches and found one (sad) ending. Still, I'm going to criticize, while acknowledging that some stuff is just due to the limitations of the medium. Just a few of my negative impressions, though my overall rating is positive.
First off, the MC is kind of an ass. The only justification for his obsessing over Helena is maybe his youth. He acts as if she has done him some great wrong, yet she rejected his advances from the start. She friendzoned him early on. She warned him against pursuing her. The only "wrong" she committed was not telling her about her boyfriend. But really, why should she? He isn't owed her life story. She didn't lead him on, he led himself on. His interactions with her are so whiny, entitled, and cringey.
Same with his reaction to Olivia. Yeah, she may be dumb tart screwing for grades. She could also be a victim, coerced into sex with her grades used as a point of leverage. The MC has no idea and instantly labels her a shitty slut. What an asshole.
After my first messy playthrough, I decided to focus on developing a relationship with one girl only. Helga is shoehorned in, even if you choose to ignore her, since dating her at least once is plot relevant. Alanna is also shoehorned in for this reason. But it makes some of the dialogue feel off when you have been ignoring Helga in favor of Ann, and suddenly you are feeling guilty because you are wronging Helga. What?
If you have been ignoring both Helga and Helena, Helena is shoehorned in again as soon as you completely reject Helga. The game really seems to want you to struggle with your imaginary "feelings" for at least two women.
The Helena interactions bug me the most. Still, it's a good game and I think the average fapster would enjoy at least a few playthroughs. I really can't get into Helena, but I'm going to try a Helga run next. I'll save Helena for last since that whole story irks me so much.
Edit: After seeing the comment above, I can't believe I forgot the Ann rape (also shoehorned in as the opening of the relationship). Yeah. That was...yeah.