Ian lost any credibility with him whining about Gillian when he could also fuck Minerva and Cindy. I would've set a flag that homewrecker Ian can still feel hurt about Gillian by any means, its very human and natural, but also has the introspection to point out that he does the same shit to others.
This chapter is the turning point in how the sitcom setting is dropped and how it turns more and more in the GGGB fuckfest in the end where everyone always has the choice to fuck anyone without any meaning behind relationships and commitment anymore.
E.g. if Ian always picks the love options with Cindy, he shouldn't be allowed to break up with her in chapter 10. The option there should only be possible if he is casual about the affair. But the games greatest strenght to have as much meaningfull options as possible becomes its obsession and greatest weakness, since restrictions and being lead on one-way paths are important.