HT, regarding the UA time, since it sounds like your W is worried about leaving the baby, I have a suggestion that my sister and her H have used to help them leave behind their toddler (the one with health issues).

They both have the iPhone4 which has the dual cameras. They leave one with the sitter and take the other. They are able to call using FaceTime and check in and "see" what is going on in the house while they are out. If you don't have an iPhone4, it may be worth looking into the $$ to upgrade (there are other models that use FaceTime, btw, not just the iPhone) if this will help your W relax enough to enjoy the date.

I think someone else suggested this but maybe you could just go out for a drink and appetizer at a bar and make it a shorter date for the first few times until she feels a little more confident about leaving the baby.

Is your W still checking in here?

Ddays 2007 and 2011
Plan B 6/21/11
Divorced July 2012
2 kids
How to Plan B Correctly
Parallel Parenting in Plan B