I made a playthrough where Ian fucked every girl at least once and it's possible to fuck Cindy without getting in love with her while still dating (but not couple) Lena who is in love with Ian but also with Holly. You get to the beach trip and instead of breaking up with Lena because she wants a more commited relationship, chad Ian gets the trinity. So IIRC, you are on chapter 13 with chad Ian having fucked Cherry (but not any more I think), Alison in thereesome with Jeremy and after Cherry's exposition, Emma (even during the beach trip before Lena arrives), Minerva (rough dominating path), Louise in a threesome with Lena and do the sexting with her after and also flirting with Ivy and I even tried late telling Cindy that I was getting in love with her just to see what happens.Going by my playthrough, at the very least Ian and Cindy can bang in the alley. For this matter you can probably prolong it for a couple more sex scenes until Lena/Cindy split point, although now am not sure if this doesn't pop up as trinity blocker, if Ian was doing more with Cindy than just the "one time mistake we both regretted" that he gets away with otherwise.
But yeah, you can in fact get both Cindy and Holly in some capacity this way.![]()
The other possibility is getting into a couple relationship with Lena and cheating the shit out of it ending up fucking slutty Holly after breaking up with Lena. But you have to make the sacrifice of making an effort to help Perry succeed with Emma. The advantage is that you can play that way without getting over Gillian and following her back in Insta so another possible future girl to add to Ian's bodycount that way.
PD: I forgot bad Jess in both playthroughs. Obtained thanks to Emma’s magic drug , of course.
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