Trump Jr. and the rest of his family reportedly grew weary of Guilfoyle’s ‘tight dresses’ and attention-seeking ways, while Anderson’s ‘Waspy,’ model looks

In the days after Donald Trump Jr. was seen holding hands with Florida socialite Bettina Anderson, PEOPLE has learned that he and fiancée Kimberly Guilfoyle have broken up

It was an announcement made amid a swirl of tabloid speculation: Kimberly Guilfoyle, a loyalist of President-elect Donald J. Trump and — more pointedly — the fiancée of his son Donald Jr., had been named as his choice to be ambassador to Greece.