My wife and I began dating in August, 1989. After 4 or 5 weeks, it was Rosh Hashana time, so I had flowers sent to her home. (She lived with 3 other girls in Flatbush at the time.) She was very appreciative, and called me right after R”H ended to thank me.
We got engaged on Thanksgiving of that year, so I arranged to have flowers delivered to her on the following Monday at her office. She was quite surprised and excited, and she had to tell everyone why I had sent them.
Of course, we were not yeshivish then (nor are we now), so the rules may be different. Are the rules really that rigid about something as simple as flowers?