Donald Trump Jr looks unrecognizable in resurfaced pictures during first marriage after engagement to Kimberly Guilfoyle

DONALD Trump Jr. looks unrecognizable in resurfaced pictures from his first marriage.

The former president's son hit the headlines this week after it emerged he had secretly proposed to girlfriend Kimberly Guilfoyle on New Year's Eve 2020.


But in images taken in 2006 he looks completely different to the man pictured at his father's New Year's Eve gala celebration at Mar-a-Lago this year.

Don Jr. was married to Vanessa from 2005 after proposing to her with an $100,000 engagement ring.

The wedding was held at the Mar-a-Lago club in Florida and was officiated by Judge Maryanne Trump Barry, Donald Trump Jr's aunt.

The couple share five children: Donald Trump III, Kai Madison, Tristan Milos, Chloe Sophia and Spencer Frederick.

Vanessa filed for divorce from Donald Trump's eldest child after twelve years of marriage in 2018.

Meanwhile, Don Jr.'s new fiancée Kimberly -who was previously married to California Governor Gavin Newsom – herself looks completely different in a throwback picture from 2004.

Former Fox News host Guilfoyle was married to the Democratic politician from 2001 to 2006. She was the first lady of San Francisco while he served as mayor.

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After they divorced, she married her second husband Eric Villency in 2006.

However, the couple announced their split just three years later after having a son together.

Don Jr. and Kimberly reportedly became friends as their children went to the same private school in Manhattan, according to the Washington Post.

Guilfoyle had been friends with the Trump family for years, and was reportedly in talks to become the White House press secretary.

Three months after Trump Jr.'s ex-wife Vanessa filed for divorce in 2018, it was leaked that the couple was dating.

The pair became serious, even buying a mansion together in Mar-a-Lago.

BOMBSHELL ENGAGEMENT

The former president's son popped the question on New Year's Eve 2020.

However, the pair kept their engagement a secret for over a year.

The news comes after Guilfoyle shared an Instagram post featuring pictures of herself and Don Jr at his father's New Year's Eve gala celebration at Mar-a-Lago in Florida.

"Tonight was extra special celebrating @donaldjtrumpjr’s birthday," the former Fox News host captioned the photo.

"Don, you are strong, smart, courageous, funny and the love of my life. I can’t wait to spend the rest of our lives together. Love you."

In the picture, Guilfoyle sports an 8-carat diamond ring on her engagement finger.


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