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The one that you can buy the Stamina drinks from wont go to the farm. What am I doing wrong?

(+1)

I got her by purchasing all of her stock, Twice. It's a huge money sink. I suggest working at the local establishment and shaking your money maker to pay for the junk in her trunk until she realizes you're the only one buying anything from her.

Yes, I made two butt jokes. No, I have no shame.

Buy her out,  sleep, then go find her again

I found the 3 cowmilks, bought all the stamina supply of the cowgirl slums, even slept.. but it still shows 5.

I also reseted (used the bell) and invited 6 cowgirls again, bought all the stamina supply, it still says I have only 5 cowgirls have joined.

(+1)

One of them doesn't immediately go with you. Sleep, then look around the slums again!