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I’m with Pam. It’s basically impossible to choose an outfit when the stakes are high.
I like her bouncing thoughts here. Very real pre-date jitters.

I love that you have Jim with rolled up sleeves. Nice touch. I like that they’re basically going through the same thought processes as they prepare for the date.

As a couple of others have commented, there’s a lot to be said for breaking up your chunks of text a little. Whenever a new person speaks, it should be on the next line. This really adds a great deal of clarity to any piece of writing.

A very sweet setup for their date. It was nice to have Jim present Pam with options and let her make the final call. A diner feels very them.

This was very cute. The fact they're both nervous about the date is incredibly endearing. However one gets the sense that despite the fancy clothes and flowers, they're still them and they're going to have fun finding their way back to each other.

Again the wall of text, for me, made it somewhat hard to read. I've often said to be a good writer, one should be a good reader. Next time you pick up a book, take a look at how the words on the page are laid out. Paragraph breaks give a lot of information as to who is talking, when they're talking, or some new important point is being made. Those subtle distinctions, for me, tend to get lost in just a wall of text.

Author's Response: Thanks for the feedback.  I am rewriting the third chapter with that format right now.