Are you touching his pecs/chest, hands, etc. Basically his "hot" areas. Take him to the bookstore, not only is it cheapest, but you can buy a newspaper and novel there while doing the recommended touching and this will boost the date score tremendously.
Talk to the stalker guy in the park if you haven't already, he will inform you about your level of relationship you're at with Tocchan. Last but not least, don't just invite him on dates, talk to him during the week; he can be found at the Agency, Mart, Bookstore and Park. Although I don't think it really changes anything, also work to do well in auditions. Money is def necessary after all.
Sad as it is to say, if it's June and there's been no real change in your relationship with him, I think you should start over.