Say, What?
I guess if a Sim from the active household, takes a Sim from an inactive household out for the Night on the Town, in which he proposes and she accepts, how is it, then, that Night on the Town was deem...
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for a long time it would reset but I noticed in one of my recent plays that sims will remember celebrating if they checked something off the list, it might still be buggy since it's not so obvious as most people give one holiday to a family. In your case I'd say she would have needed to get something else after his proposal to check it off for her. Kind of wish it stuck with different households interacting but maybe it'll be randomly updated again. Fingers crossed.
