The sorrow of it all

[trumpet]

What happens if it goes really sideways, in a ball of fire?

I love to make 15 chess moves before they happen, 'just in case'. And then I get upset/disappointed/angry when the plan doesn't work in the order I set in my mind.

Hidden/unspoken expectations.

Sounds like you're expecting them to go right. The key is to have NO expectations. How can you reduce your expectations, so that you don't put pressure on her OR yourself?

Pretend she's a buddy from long ago, and you're going out for a beer. Those kind of expectations. Of having some fun, of enjoying some company. Don't put the weight of your entire future on a night. Or the weight of your divorce on her. You might be doing that without realizing it... maybe not, but something to think about.