Dupre and Earle were first linked mere months after Dupre’s scandal with Spitzer broke. The Emperors Club VIP escort and the then-married exec at asphalt and road construction outfit The Earle Companies flirted at a Jersey Shore restaurant in 2008, prompting Earle to reportedly brag to a pal at the time, “I could have had her for free!” (Judging by the size of the diamond we’re told Ashley’s sporting, turns out he couldn’t.)
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