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As I recall, the time to do so is only available during the storyline when you are looking for a fairy for the guild, and you can only flirt with her if your reputation is high enough with Wimborn.

So best thing to do is spend several days saving travelers from bandits and not asking a reward right after you get the quest for capturing a fairy until Maple flirts with you.  I also believe that each level of flirting requires a higher reputation.

Damn, wish there was a more accurate way to tell rep. I loaded old save and killed a few bandits with bystanders. Now I can flirt, even if reputation says "Great" just like before the kills.

Pretty sure it's not limited to that time frame, just to reputation, as I thought I recruited her much later than that point.

You have to start it during the quest, but I don't remember if you have to finish it during the quest as well. All I know is that if you don't start it, you can't have it.

I was curious, so checked the code. you're right, you do have to start it while doing that quest.  However, you only have to ask about faries, nothing more.  The flirting can happen later, asking about fairies starts it out and that requires the mainquest, but the rest is independent of that. Everything requiring reputation can happen at any point after that, so just make sure to ask her about fairies when first tasked with finding a fairy.