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Michele
It's not made clear, but I took it that he was confused/upset with how difficult her life was/had been. It was less about the tool box and more about his burgeoning feelings for her and how conflicted he was about them.
Nicky
When trying to convince Diana he was serious about being with her, he told her that when he saw her pink toolbox with puppies on it, he'd never been angrier with himself for making stupid life choices. It was a sentence that was in the audio version, but not in the Kindle version.
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