A Timeline of Donald Trump Jr. and Bettina Anderson’s Relationship

Anderson was photographed sitting behind Trump Jr., Guilfoyle, and other members of the Trump family on the third and fourth days of the Republican National Convention.

Guilfoyle was still wearing her engagement ring.

Anderson and Trump Jr. were photographed dining together at the Honor Bar, a restaurant located about 4 miles from Mar-a-Lago, The Daily Mail reported.

Neither responded to a request for comment in September about the nature of their relationship.

Tickets to the fundraising dinner cost $100,000 a couple and admission to a fireside chat cost $30,000 a couple, the Palm Beach Daily News reported. Serving on the host committee of the event required a $250,000 contribution.

Anderson and Trump Jr. were photographed holding hands as they left Buccan, a restaurant in Palm Beach, on Anderson’s 38th birthday, The Daily Mail reported.

Anderson also shared a photo on her Instagram story of a bouquet of flowers and a card reading, “Many have said you’re aging out but I think you’re perfect…happy birthday!” She tagged Trump Jr. in the post, appearing to indicate that he was the sender.

Later that month, Anderson joined Trump Jr. at the Trump family’s New Year’s Eve party at Mar-a-Lago.

While Trump Jr. did not officially confirm that he and Guilfoyle had broken off their engagement, he said in a statement to Page Six that they “will always keep a special bond” and that he “could not be more proud of her and the important role she’ll continue to play in my father’s administration” as ambassador to Greece.

Anderson and Trump Jr. attended an inaugural reception at Trump National Golf Club in Washington, DC, on January 18. On January 19, they held hands and danced to “YMCA” by The Village People at the Turning Point USA Inaugural-Eve Ball.

Anderson and Trump Jr. traveled to the Capitol Rotunda together on Inauguration Day but sat separately for the ceremony. Trump Jr. sat with his family members on the inaugural platform, while Anderson took her seat in the crowd.

Guilfoyle was also seated in the audience for the inauguration, but not with the Trump family as she had been at the RNC.

President Trump was the first sitting president to ever attend the Super Bowl. He was joined by Trump Jr., Anderson, and other family members and associates to watch the Philadelphia Eagles defeat the Kansas City Chiefs at Caesars Superdome in New Orleans.

Trump Jr. and Anderson were photographed cuddling in their seats in the House chamber before Trump’s speech began.

Trump Jr. and Anderson attended the mfAR Palm Beach Gala in support of the organization’s AIDS research and global HIV prevention.

Other celebrities in attendance included Martha Stewart, who received mfAR’s Award of Inspiration, Tommy Hilfiger, and Ricky Martin.

The gala was held days after People magazine reported that Trump Jr.’s ex-wife, Vanessa Trump, is dating Tiger Woods.

That same month, they also attended a golf event at Trump National Doral, Trump’s golf resort in Doral, Florida.

Trump Jr. and Anderson were seated in front of Tiffany Trump and Michael Boulos for the military parade in Washington, DC, which featured 6,600 troops, 150 vehicles, and over 50 aircraft.

Trump Jr. and Anderson joined Eric and Lara Trump at Trump Turnberry, one of Trump’s golf clubs in Scotland, for the announcement of a new trade deal between the US and the European Union.

They were then joined by two of Trump Jr.’s children, Spencer and Chloe, at the ribbon-cutting ceremony for a new golf course at Trump International Golf Links.