I suspect everyone Harry loves will be fine and dandy, but they won't want anything to do with his mirror universe double.

 

Yeah Susan and co will likely be alive. But probably not on good terms with Harry, but he may see that as the price to pay for their lives.

 

Or evil Dresden won't even care because his decisions made it that he wasn't even that close to them. Which would hunt normal Harry even more because it would prove that it was associating with them that cased their harm.

 

I am guessing the dates will be a good portion of the book. But more of a catalyst for character growth.

My guesses for dates assuming they do 6 each:

His:
* Drive in movie.
* dinner with the carpenters
* A DND game
* camping?

Hers:
* posh restaurant
* a theatre show in private box
* intimate dinner