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Be on Dalia's path and ask for something spicy for winning the bet when being in prison on ancient Rome server. And ofc support her on the powerlifting competition and go find her after.

make sure dalia isnt grayed out in your gallery screen.  if she is, or if she grays after asking for the spicy request on semper invicta you've made too many wrong choices prior to that. 

the walkthrough in the download links will show you all correct choices and keep you on the optimal path for all girls, the harem, best ending and money management.