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If things are still the same if you have your default display set to low then the windowed mode in X-Plane won't be an option, I think X-Planes minimum resolution is 1024x768. If the default display is set to lower than that then windowed mode probably won't work.
I just tried something, changed my desktop resolution to 800x600 then launched X-Plane and indeed the windowed option isn't available, Have your friend check their desktop resolution.
How are you guys getting it to run in windowed mode?