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As I said last time I was able to have her was the christmas party but they may have added other date options with the last change.
From the WIKI Xmas party...... The party
Prerequisites: done Christmas invitation, Friday before Christmas, 14.00-18.00
During the party, Mike interacts with the girl with the highest Love.png. If Dwayne is still the CEO, he will make a pass at her and Mike can intervene. If he does, he loses 2 promotions and 10% work progress. If he chooses not to get involved, the girl loses -10 Love.png. For the special sex scene, Mike can choose any girl with Love.png >= 50 he already had sex with once.
If Mike has become CEO he can also make Cherie the girl of the evening.
Just went thru the global list and this is the only achievement for Cherie I can find. I'm guessing Xmas party sex but it could also tie into Cassidy ending paths or office possibilities she could show up for. Hope you get it worked out!
HOWEVER, I think to get this to primed up and her to come to party you have some crossover events from both the Dwayne CEO fight and Cassidy interactions where you promise not to abandon her AND that you tell Cherie you want to be with her BUT later when it counts (not just a booty call right then and there). It's sort of like a side quest that tacks on a love interaction with Cherie but not like real relationship interactions like other girls.