I went ahead and did my final post. I decided to go ahead with my initial plan even if he doesn't make it.
The game was an interesting concept, but I think it sorta fell flat for various reasons.
• I'm not always quick with ideas, and heck sometimes prompts don't inspire me. Even with a 90 minute version I think id have struggled to make up answers that were compelling.
• We didn't have music going or a timer. The urgency just wasn't there. I added a few songs here and there, but overall it felt silent compared to likely what the intended way of play is.
• The activity fizzled. Which happens in so many games. Life reasons or whatever, our group was dwindling down. With less input, and less activity, things were trending down.
• Also, I think I prefer my fantasy. I wanted to give the whole teenager irl game a go, and I think it just doesn't grab me enough.
• I liked the idea of playing the game via texts, but the immersion factor just didn't carry as well for me.
Hopefully we had some fun and learned lessons on games like this. I think I'm pretty against prompt games now. Just doesn't work as well with my sporadic creativity. Still, thanks for the game!