The second time you mentioned, she isn't trying to get you to cheat. She is actually curious as to whether or not you would share her with your boyfriend. As in let you, the MC at a point in time, be with olivia with Claire's permission. She is not trying to get you to cheat that time around, nor is she really the first time. She's actually more upset because you ruined her chance in the beginning by assuming the guys had ill intention. When they, in reality, could have actually just been trying to help. In fact, people who play the NTR route know that the men were not at all trying to corrupt the girls, but actually help them and have their own backstory.