Have let my thoughts crystallize a bit more! This was a polished and well-written game that unfortunately I didn’t really connect with, for two main reasons. One is that I was never really emotionally engaged. The PC is clearly a specific character, rather than a blank-slate/self-insert; they have these specific memories of their relationship with this person, and they’ve made certain life choices like giving up painting to work at an ad agency. So I couldn’t pretend it was actually me going through this, but I also didn’t learn enough about the PC to really give me a sense of them as a person, which left me feeling emotionally distant from them and their remembrances of the artist character. (It doesn’t help that the memories I got on my initial playthrough made that character come across as an asshole who I personally wouldn’t have kept putting up with.)
The other reason was the painting being automatically created for me at the end; it felt like the game was dictating what my emotional response to the memories should be. I would have found it much more meaningful to get to decide for myself what subject, mood, etc. the painting should focus on—being able to interpret the memories for myself, using the choices of what to paint to reflect on what I took from them. Being allowed to adjust the painting afterward was nice but didn’t hit the same way doing it myself from the start would have.