Sophie Monk and Jimmy Esebag
This odd couple were briefly engaged in 2011. Model Sophie Monk announced the surprise engagement to the much older French businessman on an Australian radio show, then announced the split a few weeks later on Chelsea Handler's show, Chelsea Lately when Handler asked her about her recent engagement to "that old guy." Ouch! Monk said "I'm newly single" and followed that up with the juicy hint that she might even "turn Samantha Ronson."
events
2011

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