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I'm in the second edit/rewrite portion after beta reader feedback and time to think about what it was missing.
Right now, the MC, Frank, is walking through the downtown after having had dinner with his boss and mentor. He's looking at the empty buildings in the Rustbelt town's downtown area while thinking about a woman he shouldn't be thinking about. This is where I show just how deep the damage in his character goes. He is, just like the downtown he's strolling through, a collection of could have been, used to be, and never will again.
Ooh, I love writing scenes like that. Also like how you described the lady as "a woman he shouldn't be thinking about." You should include that line somewhere in your novel.