Hey Guys And Gals, Here is my 100% Achievement Guide & Full Walkthrough for Wailing Heights!
Once you get to play as Lola and can turn into a bat with the
button, go to the town hall and fly up into a window (This is where you can get the first of two extra collectibles). progress the story in here and you have to throw a book outside.
Two wolves show and pick the book up, Now we can go to the back of the area to the "Ruff House" Bar where you will see at the very right hand side next to the bar one of the wolves.
Chat to him, and his friend comes in. Once that dialogue is finished, BEFORE You leave, make sure to talk to the other wolf at the bar.
He will talk all things ball, all you need to do to unlock this achievement is exhaust all dialogue options with him and thats it!
Go to 16:05 in my video to see where and how it unlocks.
Hope This Helps!