Seriously, thank you so much for making this, or at least trying :D I wanted to try this myself, but i'm completely lost, lol. You seem like you have a much better understanding of the editor. I was thinking of having the player steal something for a present, too. It's the most obvious solution to me. As for when the romance becomes available? I'd say after you finish the main thieves guild quest (after you get your Nightingale power, NOT after you become master, because that takes much longer).