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Help! I've finished Aloth's Painted Masks quest, passed Approval 2 with him, and... Nothing. I intended for my Watcher to romance the guy from the very beginning, but it seems like I missed something -- not sure if it was well hidden or what. Is there any way I can figure out if I've missed it for sure or not?

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Did you get his +2 approval conversation? That's the one where you can (possibly, with the right choices) initiate the romance. There is a bug which prevents that conversation from triggering for some folks, though.

I don't remember ever getting it. I remember hitting Approval 2 and thinking I needed to progress his quest to open up the Approval 2 convo.

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