Some thoughts in retrospect.
Here’s the game mechanic. There are 2 conversation topics that will give you a scenario for confessing but for that to happen, for each of them, two other specific topics need to have been already discussed (doesn’t matter which order), which the “confession-friendly” topic builds upon. If you go for the confesssion topic first, before finishing the other two, it won’t build upon anything and you can’t confess properly. But you can go back to the same topic after you completed the previous two.
One glaring weakness is that it’s hard to tell when it’s okay to initiate a change in topic. I blame the limits on my writing skills. In general, each topic has a point to be made, after which the discussion sort of winds down. It’s safe to change topics then.
If I were to do this over, I would have some sort of indicator to let you know how many “precursor” topics you’ve already covered, so you’ll know when to look out for an opening.