From Vanessa to Bettina: A Look Back at Donald Trump Jr's Three High-Profile Proposals

Donald Trump Jr is engaged for the third time, with President Donald Trump confirming the news at a White House Christmas event on Monday.

The president's eldest son is set to marry Palm Beach socialite Bettina Anderson, just a year after his high-profile separation from former fiancée Kimberly Guilfoyle. The announcement marks the latest chapter in Donald Jr's closely watched personal life.

Donald Trump Jr's 'Bizarre' Proposal to Vanessa

Donald Jr's first foray into matrimony began with a proposal to model Vanessa Kay Haydon in November 2004. He proposed at a Short Hills Mall jewellery store in New Jersey with a £78,000 ($100,000) diamond ring.

The proposal drew public criticism after it was reported that he had accepted the ring for free in exchange for staging a press event at the store. 'Leave it to a Trump to get the engagement ring comp'd so he doesn't have to spend a cent on it,' one user commented on X (formerly Twitter), according to the Daily Mail. Another mocked him for 'turning his proposal into an ad.'

Another mocked Donald Jr for giving Vanessa a complimentary ring and 'turning his proposal into an ad.' The same user called the Trumps the 'cheapest motherf*****s ever.' Another commenter joked that they enjoyed the part about Donald Jr not paying for the ring.

Despite the commercialised start, Donald Jr and Vanessa married in 2005. However, they were together for only 13 years, as they divorced in 2018.

The exes share five children Kai, Donald III, Tristan, Spencer and Chloe. Vanessa has since been linked to golfer Tiger Woods.

A Secret New Year Proposal to Kimberly Guilfoyle

Following his divorce, Donald Jr. entered a long-term partnership with former Fox News host Kimberly Guilfoyle. The duo immediately became the face of Donald Trump's campaigns.

He reportedly proposed to Guilfoyle on New Year's Eve in 2020 with an 'almost eight-carat' diamond ring. They kept their engagement private for a year before she subtly announced it on Instagram in January 2022.

Trump Jr and Guilfoyle have known each other for years before they started dating. Their relationship was serious and involved significant shared investments, including a purchase of £7.6 million ($9.7 million) mansion in Jupiter, Florida.

However, in December 2024, he was spotted holding hands with Florida socialite Bettina Anderson. It was later revealed that he and Guilfoyle had already separated months earlier. In fact, even if the split reports were still fresh at the time, Donald Jr and his new lady love had already been seeing each other for 'about six months' prior to their PDA sighting.

Sources told People that Donald Jr and Guilfoyle's breakup was not a 'contentious split.' It was reportedly 'amicable' as the exes agreed to move forward with their lives separately.

'It's a friendly split between Kimberly and Don Jr,' the insider added, noting that 'they've had a very long engagement [and] it was kind of in a holding pattern.'

White House Christmas Engagement To Socialite Bettina Anderson

The latest chapter in Donald Jr.'s romantic history culminated this week in a festive engagement to Palm Beach socialite Bettina Anderson. President Trump, himself, announced the news at a holiday reception on Monday, 15 December, saying, 'I have a very special announcement to make about my son.'

Donald Jr confirmed the news in a video where he was seen on stage with his father and new fiancée, Bettina Anderson. Donald Jr shared a brief detail about his most recent proposal.

'You go down there and it's like you're going to go and you're trying to ask and you're not sure what the answer is going to be. It's always a little bit rough, but she said "Yes," so that's a big win for the end of the year,' the newly engaged Trump said, before jokingly adding, 'We'll see if she's any good.'

Anderson thanked the president and First Lady Melania Trump for hosting the event, calling it 'the most unforgettable weekend' of her life.