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1.

…staring out the expansive windows at the still, slow-moving traffic outside.

Do you mean “still” as in “not moving?” Because that doesn’t work with “slow-moving.” Or do you mean it’s “still” happening? If so, then remove the comma.

Maybe either:

…at the continuous slow-moving traffic…

Or:

…at the still slow-moving traffic…

2.

The air conditioning blared, pushing a frigid draft…

I associate “blare” with sound, so this does not fit with a/c, in my opinion. Maybe “blasted” or “blew”?

3.

In it’s place was a face pockmarked with fearfulness,…

Should be “its”

4.

Being out in the boat with Charlies?

Should be “Charlie”

5.

“Well to not choose is to choose nothing,” Becca said.

This sentence tripped me up. Not sure exactly what it’s saying. Is this what you’re going for?:

“Well, to not decide is to make a decision,” Becca said.

6.

“It was supposed just to be me. …

Order of words:

“It was supposed to just be me. …

7.

…his head titled as if trying to discern…

Should be “tilted”

(I like the thought-provoking philosophical questions this story is bringing up. Looking forward to where it’s going!)

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