This definitely had an interesting idea going for it but a few things in the execution made it convoluted and punishing. I'll give a pass to it being arbitrary what options to pick, but the gameplay to do so is really tedious. The random topic generator is a neat concept but generally lead to a lot of waiting and nothing else, and timing that to when you were supposed to "end" the conversation became a bit too stressful and especially too cryptic to ever find out myself.
It was cute tho. Aggressive flirting games are always fun.