Hi Ruda,
did you try to 'gift' the pendant of earth rogue to him at the tavern with the gifting option? If he accepted then he should be waiting at the flower field. (unless you already did a bond 6 event for that day, then you have to rest before you can do another 'date'). If you didn't flirt with him enough on the bond 4+5 convos, he will reject the pendant but will accept a friendship ring. Let me know if that helps or if you have any more details or maybe screen shot that I can see if there's something bugging out.