I believe Cullen is one of the romances you can start at any time in the game once you arrive at Skyhold, and you can trigger his first kiss scene at any time (it isn't tied to any specific point in any of his cutscenes as the story progresses). The flirt during the chess scene isn't overt, either, you just say you should spend more time together and he agrees (and there's a little sexual tension underneath their formality). I think once you flirt with him during the chess scene or after--you can ask if he's taken-- is when you can initiate their first kiss scene.
I'm not an expert on his romance and haven't finished it yet, but this is what I've picked up so far.
Thank you for the input.
Ooh, the chess scene. Polite, formal, and subtle, but effective? That sounds perfect, actually. I'll keep that in mind. =)
I cannot never NOT flirt with him (lol!), but I have heard someone say they romanced Blackwall all through till the end (of that romance), broke it off with him, and then got Cullen. BUT, I am not sure if they had been flirting with him some as well...so...not sure...
Have you had the chess scene yet?
Thank you. I have seen the chess scene, though I won't be able to put it to good use till I make a different character (who hasn't flirted with anyone else) in a different playthrough.
The Cullen and Josephine romances work differently than the companions. To get into a relationship with them you typically have to take ever flirt option you get when compared to companions which work through approval. If the tarot card has changed with the character you have been flirting with the most then you are locked in with them and it is too late to get into another relationship, but if the tarot card has yet to change then you are good.
Uh oh. Does that include Haven? I've talked to him in Haven a couple of times in this playthrough, saw the flirt option, but ignored it because my elf was secretly thinking, "You are a Templar that imprisoned my fellow mages and supported a church that demonizes and outlaws my people's religion. Like Hell I'm interested in you!"
If I don't click any flirt options at Haven but do so by Skyhold, would that work out?