If he gets close enough to Supergirl to take a good look at her, he could easily realize that she bears a striking similarity to Kara.
Still, Cat came to count Supergirl as a friend, and she really didn’t want to expose Supergirl.
Cat Grant came close to discovering Kara’s secret throughout Season 1, and Kara had to resort to some pretty extreme means to avoid discovery.
She certainly demands plenty of his attention as his employee, and he’s an observant man.
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