I think you just need to win at Old maid once to go outside with her that's what I did and the option to talk to her was open.
This was the solution, i've tried all sorts of clothing, but once i won at Old maid the dialogue was available
its simple to do it you need to quick chat with her several times after triggering the annalie is event. like you need to increace you bound with her trought chatting or playing card games
