it's okay i guest..
as fare as i remember, i've seen that event when cliff's heart is already red..
,so you just have to wait for winter and see that event on the rose square..

I triggered it before, it was after Fall Harvest and I think it is about Manna and Duke,
arguing. Go to the Winery on an Tuesday, Thursday or Sunday between 5pm - 7pm.
Duke is about to enter the winery around 5pm, so if you enter before him you won't see the
event he has to be insinde so get out and wait for him to enter and go after him.

Hope it helped!!!^^