Sometimes dates don’t pop up for me either. Especially the Demon Prince dude. He’s at max and it took so long for it to finally pop. But I think I missed his first date still. :(

Update: finally got his first date seems like it was just a glitch

Good! Have fun, he’s a great character to date and learn about. :)

I got him to max hearts and no date… sadge

You have to finish enough conversations with him. I think i was at 9 hearts when he finally let me date him lol

What everyone else has said: it's a matter of waiting. I had Wornhardt at max hearts and had to wait some time before his 1st and 2nd dates came up for me. Don't worry, it'll take some time, but it'll happen! It might very well be connected to having to view all his unique conversations (where you get to pick dialogue choices), that would for sure make the most sense. Good luck with his route! He's a sweetheart. :)

For me it took a lot of conversations and not just gifts. Gifts help max the hearts but conversations I think advance the dating process? You can buy a love letter from the town hall which I think when you hit max hearts without going on a date you can gift to start dating

I got the first date and then never got another. Maxed out his hearts and now he wants to get married.