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Ok, I have pretty much everything done, the leads are complete, heart cards are maxed, I'm in act 2, I have max education and college authority, etc... But, I'm wondering, how do you do the naughty with the big 3? Whenever I ask Madison, it says that I can't go any further in this version of the game. Am I dumb? Or is something behaving weirdly?

Well, you seen to be pretty much done. 

Like, the only content the PTA moms have is that you can have a private meeting with the mother of the pool twins (blonde one). 

And in the next update you just get an extra scene with for the mom and scenes with the twins. 

Then how do you do the private meeting with the mom?

(+1)

Talk to Madison about it.

How? The only option remotely related to that is "ask about the big 3" and that just says that I can't do anything else in this version.  (im on version 14.1 btw)

Uhhh, weird.

So when you have authority level 3.
* You try to increase authority, it fails.
* You talk to Madison to get the PTA moms to go to your club.
* You succeed in getting them on your side.
* You try to increase authority, it works.
* You can now talk to Madison again to talk more to the PTA moms, starting with the mother of the pool twins.

I don't know why it wouldn't work.
The event was added on 0.14.1 having a continuation on 0.14.2

Weird.