As I have become more aware of the popularity of Dorothy, I have made a little video of one of her courtship Events in Rune Factory 2. You will find 'Heart Events' in Rune Factory 2 to be quite different from those in other Harvest Moon games. Often when you have a choice of responses, the one you choose will not affect the girl's heart level, even if it appears to be a 'negative' response.
'Heart Events' are experienced when you accept Requests from the Eligible Girls. In this event, Dorothy requests that you meet her to try her Chocolate Cookies. In the course of the event, you have a choice to pronounce the Cookies either to be 'good' or 'awful'. It is by accepting and completing the Requesty that the girl's heart level is raised. Even if you tell Dorothy her baking is 'awful', you will not lose any affection with her. In fact, this response leads to a very amusing result, one that may be more interesting than that experienced if you make the 'positive' response.
The video shows both results.