Well yes her date mechanic is slightly more annoying compare to the other girls especially for players that went in blind (no guide or walkthrough) like you (& me). With enough trials & errors, i can safely assume it depends on your actions with her during the date. There're 3 different periods; hug & kiss, kiss & touch OR touch & kiss, then touch & lewd. After you've touch & lewd her & get a kiss at the end & get invited to her place, then it should count towards a successful date.Nope. It happened in the last event when the game told me to have 2 successful dates with her. I had to go on something like 15 dates until it triggered. This is after that when the game tells me to have 4 successful dates. I don't know how to trigger it this time.