What? I said nothing about Ian needing to be a loser. My first paragraph was agreeing with you and @SearingFive, my second paragraph was an aside comment about the actual corruption.
Then it seems to be a misunderstanding, since for me it sounded as if Ian has to be loser here, which isn´t the case.
We have three major variants of Holly in the game so far. One is "super-nerdy" Holly, which is her base persona at start. Ian and her can get together only rather early via the book travel. AFAIK a later option to get together with this Holly hinges very much on several factors and is complicated.
Version 2 of Holly is "encouraged" Holly. You can get her either by being in a relationship with Ian, who deftly encourages Holly to be more bold or by Holly wanting to learn how to attract Ian by being more like Lena and Ivy, but keeping Ivy´s influence low. This the more forward Holly we can see at the beach holiday, e.g. wearing a bolder bikini and still have a Schopenhauer book with her. I even got that once with a slightly slutty Holly, when I kept Ivy influencing Holly but on a low level.
Also had a path variant with Ian and Holly already in a relationship and Holly having the erolit book with her.
Version 3 of Holly is slut Holly, who you get by Holly wanting to learn how to attract Ian by being more like Lena and Ivy and letting Ivy influence her a lot. As I said, it seems to be a late variant to get together with Holly. This is rather clear by dia/monologue. Slutty Holly is obviously after Ian by her statements during the beach holiday and some Ian variants recognise this version of Holly rather positively.
As mentioned earlier, I theorise that if Ian and wild Holly become a couple after the beach holiday, this will mostly end Ivy´s influence on her. Since Holly now got Ian, who she wanted from the start, she would see no need to become sluttier/wilder. Not for nothing it was how she is now which brought her and Ian together, at least she thinks so (and is right up to a certain point).