Unless he commits to Ashley, he is always a free-spirited player hanging around in VIP lounges for girls to score with.
Holly must be under Ivys influence, musn't be with Ian and Lena must've fucked Robert. Then she and Ivy can hook her up with Robert and they fuck around chapter 12.
In a certain way Robert is THE lucky beggar of ORS. He can potentially bed Lena and Holly, something very few others of the main characters can do.If Lena sleeps with Robert in the early game you can introduce him to Holly in chapter 12 and they end up banging.
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This is tempered by the fact Lena can put him aside and Holly slutted around with a plan not necessarily including him in the long run. Wild Holly released her inner slut to become more attractive to Ian (believing he prefers wild, slutty girls as GF) and if Ian and her become a couple now in late ch.12, I doubt Holly will stay quite as wild since her plan functioned well.