You're welcome. Yeah Lena and Ivy can make Holly bolder without sleeping with them or cheating on Ian. You get more options for that if you have her join pole dancing and Lena can help keep Ivy from pushing Holly too far as well.
In addition Ian can also help getting Holly being bolder without cheating and stuff. And while it is really great that Ian, Lena and (to a certain point) Ivy can help sweet Holly becoming bolder without her cheating on Ian or Lena, it would also be great if there were a path where Ian and wild Holly can become a dedicated couple. And a confident Ian at that, who likes Holly being slutty.
So in essence a "medium" path for wild slut Holly. Instead becoming more and more like Ivy, finally getting into a relationship with an Ian being ok with her being a slut(which was her push to being bolder, getting Ian to "see" her) would keep her wild, but with a red line this Holly would not cross because she now got Ian, whom she wanted to begin with.