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Checked the log think only thing on their involving her was taking like 100 pics or something. Would help if knew the difference in the Angel Symbol and Heart symbol.  I ended up getting the angel atleast 30 times. Then started trying for the heart one. Which seemed like would always tick her off so originally why never tried.  Wasn't sure if was actually a broken heart. Ended getting it like ten times. Then eventually gave up.  I have like 300k now getting really bored.  Ended up banging her sister and a few others. Which really wasn't that great tbh. When all were three inch photo's  of a set of three. The goth girl half naked in bathroom before pics was cool. Same for the futa when bench pressing the rest are just very dull. Not really motivated to play it any further. 

Angel and devil are for the Slut and Lover Paths They are just for which path you want to go. All the scenes are like that, It´s a set of pictures. But i´m not sure how you´re not progressing with Anna´s hearts.. Would help if there was like, screenshots or something to go off of to see where you´re at. But you can also refer to this guide. Has EVERYTHING you need.

Starmaker Guide and FAQ