I documented the following Event with Dorothy in great detail for all her fans. Like Yue's Request for a Date at 9 Hearts, the 'Date' with Dorothy consists mainly of an Interview, a series of questions and responses. You have the opportunity to choose the questions you wish to ask, as well as the chance to choose different responses to her questions.
The 'best' results are given first, but I have included all possible results after that as each provides a few details about Dorothy herself.
As I have stated in other posts that deal with Romantic Request Events, I really do not think that the response you give affects heart level. It certainly does not have any substantial effect. It is by accepting the Request and satisfying it that you increase the Heart level of the individual. When I give the 'best' responses, therefore, they simply are the responses that please the girl the most, but you can give any response you like and still move forward in the Courtship.
As in your date with Yue, there is a moment when you may become very excited, thinking that you are about to experience something new. In Yue's case, it was the chance to travel to a new location. In Dorothy's case, it is the chance to see her face!
I will not spoil the surprise here, though. All will be revealed in the Event itself:
This Event leads to a new Request on the Bulletin Board from Gordon.