I don't think it depends on if your Ian is sleeping around with other Girls because my Ian does this too and there was no Indication from Alison about a possible Threesome. It really depends only if Alison and Jeremy are hooking up in your Game or are still hooking up in Chapter 9 (since Alison can stop their thing if you play it a certain way)in my saves where ian sleep with lena and with alison, yes she talks about jeremy about a threesome too. basically the premises is if ian does sleep around with other girls besides alison, alison will see ian as a sex friend and she will ask ian if he's fine with her sleeping around too. but in my main saves which ian only focus on alison, there's no trace of alison speaks about jeremy and she speaks about her relationship with ian earnestly.
since the first time this game has come out, i always play the alpha and the final version, and i've never encounter any problems at all. i think it's just because this game is so complex with the choices that a lot people might miss a lot of path.
My Ian is kind of sleeping with all possible Options right now but still keeps Alison for himself so there is no Threesome Possibility with Jeremy. I think in this Scenario this will only be possible if Ian convinces Alison in a future Chapter.
EDIT: Well now after also playing this with the Holly-Playthrough this sadly seems different
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