Keep spending time with him on weekdays even if there's no events from it. I had the same problem with that last star but eventually he confessed after around a month of constant stalking for my playthrough
What I did was to get a pet and the cheapest pc asap. Use the pc to up VA stats and play with the pet when stress hits 40. I then used the daytime on weekdays to stalk the guy. Relying on auditions for the cash only after Toru apeared.
If i recall right he confessed around mid july after stalking from Jan to Jul... continue stalking after to get Toru's back story (not sure if necessary)