On the forceful path, it seems like we have to choose between Helena and Ann. As I was playing, it felt like there wasn't a natural way to end it with one of them. There should be a significant scene that addresses the issue. In the morning with Ann, you can end the relationship and shes just like alright.. and MC is like meh. If you don't say anything, she will say shes sick of this when you come back from the date with Helena, and the MC going meh again. If you want to drop Helena, you need to do it in a really petty way by "not forgiving her" or on the next opportunity, after you have all the conversations about the future together, tell her that you want to "end this relationship" and shes like meh. You are not even in a relationship with her at that point.
Ann is a sex friend as she pointed out. It becomes obvious that she wants something more and she is a bit more serious about relationships than she let on at first, but you never have a sincere conversation with her about wanting to make it more than just sex friends. Its a bit jarring that she reacts the way she does. There needs to be a scene where she wants more from you, and there needs to be a bigger scene when you end it with her or when she is ending it with you.
As for Helena, there should be a way to remain in good terms but not pursue a relationship with her. MC already knows his reaction to her actions were not entirely justified, and she knows what she did may have been hurtful, but neither of them really did things with malicious intent. It looks like a classic case of misaligned timing in a relationship. MC shows interest in Helena but shes dating Vlad, by the time she dumps him, MC had developing feelings for Ann. He should be able to talk things out with Helena in a better way than what we are presented with here.