I knew that there was something else that I intended to mention about last Tuesday night's cafe night. Because it was the 200th, and my wife had gone to the 100th with me, I had hoped that my inlaws would take our son overnight so that my wife could go with me. My wife appeared to also like the idea, and seemed to want to go.
On the Sunday before, my sister in law (wife's sister) came up from Sydney to visit her parents for a few days, bringing her toddler (our son's cousin) with her. While our son was welcome to go and visit during the day, we were assured that his presence would guarantee that his cousin would be too hyped up to go to sleep, and therefore the option of having him stay there overnight on the Tuesday night no longer existed.
I commented to my wife that every time I ask our son if he wants to go somewhere with me when I'm in girl mode, he says no. With nobody to take him for the night, the options were that she stay home with him as usual, or that they both go with me. It was school holidays, so it wouldn't matter too much if he was up late, but I didn't want to pressure him, so it was her decision.
My wife's decision was that we all went. She told our son of her decision, and he didn't argue. When it was time for him to get ready (when I was mostly ready), I told him that it was time to get ready and he changed clothes and got ready without any fuss.
Aside from being bored (I only remember one other person going out of her way to talk to him while we were there) and tired because we were out later than he was accustomed to, he coped quite well.
I'm not sure whether it was a good result in terms of him being more prepared to go out with me when I'm en femme in the future or not, but it didn't appear to be a bad result.