I think what might be happening is that you have to do them in the same run, and you can get more of them by talking to her when she is lying down with Jenny.
I'm having a really hard time getting all 3 in one loop. I can get Jenny and Cassidy, but I can't ever seem to get Haily's event.
Haily's even can be overwritten by her own picnic event, so you may have to lower her corruption level. Alternatively Lin's will work quite well.
