Fiancé #1: Nicole Jaracz
2007 was a major year for Drew Carey. He not only replaced the irreplaceable host of The Price Is Right, Bob Barker, but he also got engaged. Carey proposed to chef Nicole Jaracz, whom he met a few years prior. The couple never made it down the aisle, but at least they ended things amicably in 2012.

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At the time, Drew’s representatives told People Magazine that they “still have a great deal of love and affection for one another… He will still be very involved with their son’s life.” Conner is Jaracz’s son from a previous relationship and Carey remains close with him to this day.