I think something similar has come up
when I asked my sister about Eva's problem, both times I only had the option "Yes"
In all other conversations, I only had one option in the submenu (the option to return was missing)
and with Jane, I still don't have the option to ask about the possibility of earning money (I assume I meet the necessary conditions)
I'm assuming that the second option is missing from the conversations this time.
(probable conditions under which I encountered it: wearing a chastity cage after the very first penis reduction)