When you get to Flotsam and after you are introduced to the monster and Sile, you go to the top floor of the INN and talk to Sile, during the conversation you have the option to say that you want to get to know her better because you guys are working together, then eventually you say you like her, and have the option to pursuade (im thinking for romance), has anyone done this? because i tried to pursuade but it said failed. Im not sure if its because i havent used pursuade yet up until that point and have only used intimidation and the AXII sign.
Hmmm..... Right after you save Dandelion and Zoltan, u guys meet up in the INN and talk for a good while, then a guy comes in a yells "the beast is here" and everyone goes outside to the harbour, after that Triss introduced Geralt to Sile and she says come to the top of the INN to her room.
When you go there you have the option to say exactly "can we talk about something besides business?" then "do you usually hunt beasts?" then "No its fine i mean i like you." then "Do you travel alone?" then you have the option to use persuade and say "You gotta learn for yourself."
I persuaded her successfully. She wears makeup when you go to kill the monster and is a little flirty, but that's about all that has happened so far. It might open something up later in the chapter/game, but I don't know.