I chose to date Nyra, Florrie, and Imogen and I seem to have gotten stuck in a loop. After Nyra's date Avery says "the second date is over" and then the next date is with Florrie, after which I just get back to a second (identical) date with Florrie. After answering her "Are you glad that I picked you?" question for a second time, there is no option to progress.