Jennie needs to reach a certain point. This will have been made a little clearer and work properly in the next update.
Bridgitte needs to see your lust for bigger women play out a little before getting comfy enough to bare her all.
Did you find everything in the kitchen and the common room? Did you check if Jimbo could be of help? There is more than one treat he sells.
If you are stuck far in, Jennie may have hinted at wanting something specific before she will keep on eating.