I think that Jeremy fucking Lena is worse than Ian fucking Louise in the threesome. My reasoning is that Ian tells Jeremy about it almost inmediately after happening while Jeremy takes a really long time to tell because Lena tells him to shut up, so he priorices Lena over his bro Ian. And Jeremy's case is potentially worse if he fucks Lena after Ian telling him that he has serious feelings for her, while Jeremy doesn't give a fuck about Louise no matter your choices as Ian or Lena.
Now Ian hiding the photoshoot and fucking Cindy makes him a worse friend to Wade that anything Jeremy might do. But Ian is Wade's friend, not his bro, so Jeremy is still the worst bro ever

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Emma's case I think it's no so clear cut, Perry has done nothing about it for years and Ian has also known her for the same ammount of time and has the same right to feel something for her and act on it. Of course if you tell Perry that you are going to help him with Emma and end up fucking her, that's pretty scummy.
But at the end of the day Ian is the MC, so morals and perceptions are around that.