For his father’s Inauguration Day events, three women who loved Donald Trump Jr. came together to celebrate Donald Trump’s second term in office. Sometimes they were in the same room.
Donald Trump Jr., son of Donald and the late Ivana Trump, has kept a steady stream of excited posts on Instagram and X about Inauguration Day and Trump’s return to the White House. When his dad got the party started early − the inaugural ball, President Trump’s Celebratory Victory Rally in Washington, D.C., on Jan. 19, 2025, and a candlelight dinner at the National Building Museum − four out of five of Donald Trump’s children posted on their respective social networks about the Inauguration Day festivities.
But if you’re looking for fresh posts related to Donald Trump Jr.’s love life, keep scrolling: Donald Trump Jr. typically posts about his five children with ex-wife Vanessa Trump, his father’s politics, his interests or podcasts. Donald Trump Jr. has not posted anything recent about his ex-fiancee Kimberly Guilfoyle or new girlfriend, Palm Beach, Florida, socialite Bettina Anderson, as an Instagram Story, Instagram Reel or Instagram posts. Donald Trump Jr. has posted plenty of Reels of his eldest daughter, Kai Madison Trump, and her adventures on the green − she’s an avid golfer (like her grandfather) and intends to attend the University of Miami in fall 2026.
Kai Madison Trump, who has 1 million followers on Instagram as of Inauguration Day or Jan. 20, 2025, posted on Instagram, an Instagram Story and Instagram Reel photos and video of her at the White House for Inauguration Day festivities. She is seen posing with her mother, Vanessa Trump.
Kimberly Guilfoyle, who was with “the love of her life” Donald Trump Jr. for six years, attended the candlelight dinner and shared a photo from the event. “It has been reported but not confirmed” about their breakup.
Rumored new love Bettina Anderson danced on stage with her reported boyfriend to the Village People’s “Y.M.C.A.” at the celebratory victory rally in D.C.
Below is more information about Donald Trump Jr., Bettina Anderson, Kimberly Guilfoyle and Vanessa Trump.
Who is Donald Trump Jr.?
Donald Trump Jr., the eldest child of Donald Trump and the late Ivanka Trump, was born on New Year’s Eve, Dec. 31, 1977. His siblings are Ivanka Trump and Eric Trump, half-sister Tiffany Trump born to Donald Trump and Marla Maples, and half-brother Barron Trump, born to Donald and Melania Trump.
Donald Trump Jr. previously was married to former model Vanessa Trump from 2005 to 2018. They have five children: Kai Madison Trump, Donald Trump III, Tristan Trump, Spencer Trump and Chloe Trump.
Donald Trump Jr. and Kimberly Guilfoyle started dating in 2018 after his divorce was finalized from Vanessa Trump. The pair were engaged and bought a house together in 2021 and split sometime in 2024. Though some news reports, including a column from the Palm Beach Daily News society columnist Shannon Donnelly, suggested Donald Trump Jr. and Guilfoyle broke up before Easter 2024, Guilfoyle posted “happy anniversary” love notes to her Instagram followers about her “soulmate” Donald Trump Jr. in April and May. She also appeared by Donald Trump Jr.’s side multiple times throughout his father’s 2024 presidential campaign − including the high-profile Republican National Convention in July 2024 and on Election Night at the Palm Beach County Convention Center in Palm Beach.
Donald Trump Jr., in turn, posted an anniversary message to Guilfoyle on April 24, 2024, to his Instagram followers: “Happy 6 year anniversary @kimberlyguilfoyle thanks for always being there no matter what the haters are throwing our way. I love you.”
In December 2024, Donald Trump Jr. was publicly spotted with model Bettina Anderson of Palm Beach, Florida. The pair attended Donald and Melania Trump’s annual New Year’s Eve party at Mar-a-Lago and Inauguration Day 2025 festivities.
Who is Kimberly Guilfoyle? Are Kimberly Guilfoyle and Donald Trump Jr. still engaged?
Kimberly Guilfoyle is a former model, attorney and Fox News host from San Francisco, California. She’s been a familiar face in the Trump circle for the past six years. Guilfoyle previously appeared on “The Five” and “Outnumbered” on Fox News. Before her relationship with Donald Trump Jr., Guilfoyle was previously married to California Gov. Gavin Newsom, a Democrat, for four years while he was the mayor of San Francisco. They divorced in 2006, and she married furniture heir Eric Villency the same year. They had a son, Ronan Villency, but divorced in 2009.
Days after photos of Donald Trump Jr. and Palm Beach, Florida, socialite Bettina Anderson were published online, Donald Trump appointed Guilfoyle as ambassador to Greece. Her ambassadorship starts Jan. 20, 2025.
The news was in the same week as breakup reports with Donald Trump Jr. On social media, Guilfoyle had consistently referred to her former fiance as her “soulmate” and “forever best friend.” Though the pair reportedly called off their wedding, a Jan. 20, 2025, check on Guilfoyle’s social networks show that she kept the photos and love notes to Donald Trump Jr. on her feed.
According to a Jan. 20, 2025, record search, Donald Trump Jr. and Kimberly Guilfoyle’s home in Jupiter is off the market and both names appear on property records.
Who is Bettina Anderson? When did model and socialite Bettina Anderson of Florida start dating Donald Trump Jr.?
When it comes to Palm Beach society, model and socialite Bettina Anderson is a well-known figure. She has an Instagram following of almost 58,000 as of Jan. 20, 2025, with lots of photos and Reels touting designers and her entourage.
For years, Anderson has attended Palm Beach society events. She also co-hosted an invitation-only Trump fundraiser in October 2024.
Photos of Anderson kissing Donald Trump Jr. were posted in December 2024 on British tabloid sites. US Weekly also reported Trump and his longtime live-in girlfriend, former Fox News host Kimberly Guilfoyle, split and called off their wedding before the presidential election in November 2024.
Since then, Donald Trump Jr. has been spotted in public with the socialite. The pair vacationed together in Italy, they attended Donald and Melania Trump’s annual New Year’s Eve party at Mar-a-Lago in Palm Beach, and the couple attended President Trump’s Celebratory Victory Rally in Washington, D.C., the night before Inauguration Day.
She has no children and lives in West Palm Beach, Florida.
When did Donald Trump Jr. and Vanessa Trump divorce?
On Nov. 12, 2005, Donald Trump Jr. married former model Vanessa Kay Trump, formerly Vanessa Kay Pergolizzi. Donald Trump introduced Donald Trump Jr. to Vanessa at a fashion show in 2003. The couple married at Donald Trump’s Mar-a-Lago estate in Palm Beach in front of about 370 guests, reports show, with the service officiated by Donald Trump’s sister, Judge Maryanne Trump Barry. Donald Trump Jr. and Vanessa Trump were 27 years old when they wed, weeks before they both turned 28 in December 2005.
Donald Trump Jr.’s siblings were in the wedding party: Ivanka Trump was a bridesmaid, and Eric Trump was a groomsman.
Vanessa and Donald Trump Jr. had five children together − Kai Trump, Donald Trump III, Tristan Trump, Spencer Trump and Chloe Trump − before they eventually divorced, after 12 years of marriage, in 2018.
In 2018, Donald Trump Jr. began dating former Fox News host Kimberly Guilfoyle. When the couple split in 2024, Donald Trump Jr. began dating Palm Beach, Florida, socialite Bettina Anderson.
Sangalang is a lead digital producer for USA TODAY Network. Follow her on Twitter or Instagram at @byjensangalang. Support local journalism. Consider subscribing to a Florida newspaper.
This article originally appeared on Palm Beach Post: Kimberly Guilfoyle, Bettina Anderson, Trump Jr. on Inauguration Day
