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That said the Cassidy thing is a likely problem and is best to try not to trigger the start of that path first, Sam on the other hand and Bree I believe are both okay to date in Emma's book.
Here is the page link for ease of reading
https://love-sex.fandom.com/wiki/Emma
Didn't go to work at all on that file so maybe that's it.
I didn't work so no Cassidy, I only had coffee with Bree, which by the wiki Emma likes, Bree and Emma get it on during the sleep over so. Emma's ok with Bree. Never had a girlfriend, passed that check with Emma, as I said got right to the end, where Emma lets MC perform oral was asked to become her boyfriend etc. but still MC could only kiss the puss.
Then how would the achievement unlock, yea Emma kissed MC 3/4 times but... Guess it doesn't really matter, I've now kissed and have had coffee with all girls except Kylie, and going by achievements, I haven't been with half of them ;}
I have all the harems active or finished (in the best possible way) all the girls at max love and kinky and all possible sex slaves at the moment in the same playthrough (working on Harmony corruption now), but lost Emma. She didn't leave for good, but her Love is locked at 12. Maybe she can be "re-dateable" in some way.