[quote=@Turboshitter]
<Snipped quote by Takashi>

Ah, perhaps they met as kids when he drew a portrait of her for the family!
[/quote]

I like that idea. That could be how he got the attention of Baron Dupoir. His father was doing a job for Lord Anzivino, and had to bring Telio along for one reason or another. Telio meets Fiametta on the estate and offers to draw a portrait of her. Maybe he sees her practicing with a sword and wanted to draw her in a "cool pose" or something.