Spoilers ahead, for those of you reading comments before playing.
I like how you set up the nonlinear storytelling. There’s a feeling of “you can only experience so much before things are over and you can’t go back” that works with the dead sister story, though I think you could’ve leaned into it harder. From what I saw on the two playthroughs during the stream, the story was smooth no matter how you ordered the objects, and you have the relationship that continues to build between the characters as you pick up more things, giving some sense of movement towards a destination.
Toby’s obliviousness concerning his friends is a funny joke, but it overstays its welcome, especially when you go back to read more than three item stories. It comes up every time you pick up something (I think? It’s been some time.), but it doesn’t have the depth to sustain that level of attention like Bart’s story does. The framing of Toby bumping into Bart so he can have an audience for his stories isn’t as well-developed as what Bart has to say about the items and his sister. It’s a romantic fantasy to meet-cute with a bear and then go on a date and have him pick you up and be embarrassed about his condoms, but that plot and the dead sister plot are so unrelated that Toby’s presence is something of a distraction. Would it be a more focused story if Bart just tripped on a rock or something and had to pick up his things while monologuing to himself in his head/to his sister/directly to the reader about what these things mean to him? Hypothetically, I guess. The art does a lot to show Bart and Toby together, and Bart does gain something from having someone listen to all his stories, but I think the story as a standalone could stand to do with either much more or much less of Toby.
The game page says it’s a demo, but I’m a little lost on what would come after. Bart continues to pick items, but it’s at his sister’s funeral? Toby’s and Bart’s relationship gets more focus?
Also the graphic on the game page is pretty, but with the text and the background opacity as they are currently, it’s a little hard to read the description and comments.