I've actually tried all three of those things in the same run and I got friendshiped again, I think I have to talk about his date? Possibly? Idk I'll have to test it out
Viewing post in Midnight Train: Going Anywhere comments
Try following this play through, the romance end is reached near the end of the video!
https://www.youtube.com/watch?time_continue=721&v=p6B9X5CF6eU&feature=emb_logo