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I did have a romance with him :) Without spoilers: there is an encounter when you first enter Moonrise Tower. Chances are - you'll need long rest after it, and then I got the projection scene with Gale.
After inviting you to meet him, you are prompt to choose supplies for the long rest, you need to do it and then it all happens.
You need to pick up "imagine kissing him", that would trigger the romance, anything else doesn't trigger it, I am pretty sure...
Fret not, romance does happen, but a bit later, in the Act 2. Just make sure to take the long rest when everything points towards the big fight.
I know it's a long wait, but it actually makes sense with him.
Also it continues in the Act 3, depending on your choices and actions.
Seriously though, most people have problems with him being super pushy with his advances, no idea why you would have trouble getting it to trigger.
I did take the long rest after the entry battle at Moonrise and before jumping down the rabbit hole after the white hare. The scene did not spawn. As mentioned, I went back several hours (many saves back) and replayed through those hours twice, still no scene. My guess is that he needed to die and be revived with the pouch he tells you to use in Act 1. He never died in my 2nd playthrough. I flirted with him and he never died. Those are the two differences between my first playthrough where the scene did take place and the second playthrough where it did not spawn.
Has anyone had a playthrough where he never died and you still got the private scene to spawn?
Yes, he has never died in my current playthrough and I never used the pouch on him.
I think what's important is to get a small scene after the first fight in Shadow Lands? He tells you that you look great, all battle-weary and such. I assume it's kind of a promise/trigger for the later full romance?
Also, I think you need to have the rest before the big battle at the Moonrise entrance, not even when you face Ketheric. That's when it all happened. And next morning it was the big battle.
So, if you refuse Wyll's kiss nothing happens? I've seen the bugs with this romance and if it happens to me, I'm going to cry.
Because Wyll made me the scene without having him in the team and almost without talking to him xD