Not having context, I assume you mean that you think you are stuck in the q&a "timed" thing. If that's the case, the timer bar is wrong. You have the same number of questions as you would in the park (6?), but the bar appears to be drained after 4 and you may think that things are stuck in a loop. Just keep asking until the real counter runs out.
The Anne date is probably still truly bugged based on a post a few posts back. That one has been bugged for a while and this dev is focused on sissification and not alpha male behaviors.
On that note, I find it extremely funny that I can have MC go on the sissy route with a 9.5" cock. On this playthrough I had them start with a larger cock and had actually taken Sandra out to the club dancing first before doing the panty raid much later in the playthrough. MC had learned the proud spell and had used a few fighting victories to spell themselves out further than that starting point. So first question is whether there are XL size chastity cages coming out of whatever city in China that specializes in sex toys. Would that be Shenzen or maybe some factory next door to Wuhan where they are squirting out nuclear attack subs? Then we go in for a leg waxing and have Asa trash talk our "micropenis" while we are pistol whipping her with it. She must be literally playing the ponies down at the race track.
got the same with Diana at the Fast Food Joint