Don Jr & Bettina Anderson's Relationship Timeline, Explained

Months before Donald Trump Jr. and Kimberly Guilfoyle called off their engagement, Donald Trump's eldest son appeared to have moved on with a new flame. Despite trying to keep his budding romance under wraps, he and Palm Beach socialite Bettina Anderson (who lives a seriously lavish life) were spotted getting cozy all around town. While it is not known how they first met, Anderson is actually close friends with Don Jr.'s ex-wife, Vanessa Trump, whom he divorced back in 2018. Therefore, it may very well be that his ex introduced him to his future girlfriend, but as strange as that may seem, it's their messy relationship timeline that's really raised eyebrows.

The Daily Mail first caught Don Jr. and Anderson canoodling in August 2024, but according to sources, he and Guilfoyle hadn't actually called off their wedding yet. "Don and Kimberly broke up before the election and started to divide assets around the end of September," an insider told Us Weekly. That would place their split after Don Jr.'s initial dates with Anderson. Even so, the source maintained that there was no drama between him and Guilfoyle. "The breakup was amicable and so is their relationship today," they assured. We may never know if that was really the case, but we are certain that Don Jr.'s latest fling has had an unconventional timeline.

Two months before Bettina Anderson and Donald Trump Jr. made headlines with their clandestine romance, the socialite was spotted sitting with the Trump family at the Republican National Convention and, at one point, was in a chair right behind Don and his then-fiancee, Kimberly Guilfoyle. The event, which was held in Milwaukee, Wisconsin in July 2024, marked the first time the duo was snapped in such close proximity.

It's unclear how Anderson made the guest list, as Page Six noted she'd only ever made one small donation to the GOP in the value of $2,800 to support Florida Republican Maria Salazar in 2022. However, a source told the outlet it was actually Don Jr.'s ex-wife, Vanessa Trump, who invited her to attend. Vanessa is apparently close friends with Anderson and, indeed, they were seen chatting at the RNC. What's more, Anderson was seated next to three of Vanessa and Don Jr.'s kids, although insiders pointed out that her seat was not assigned, but rather an "open" chair.

Anderson's friendship with Vanessa was confirmed later that August when the Daily Mail obtained photos showing the ladies intimately sharing a patio chair next to a fire pit during a party in Jupiter, Florida. Don Jr. was also in attendance, as was his eldest daughter, Kai, and all four appeared to get along well. The only person who was noticeably absent from the bash was Guilfoyle.

Kimberly Guilfoyle and Don Jr. split rumors became rampant in September 2024 and by mid-month, the Daily Mail appeared to have proof that Don Jr. was moving on. While Donald Trump's eldest kept mum on the matter, it was hard to deny what the tabloid's images showed. In the snaps, which were taken in August, he and Bettina Anderson could be seen having brunch at The Honor Bar in Palm Beach, Florida and getting cozy. "She seemed totally smitten with Don – and he with her," an onlooker told the mag. "They were definitely on a date." The lovebirds were reportedly spotted kissing and the insider added that their fling was essentially an open secret in Palm Beach. 

Even so, a source told the Daily Mail that Guilfoyle was "blindsided" by the images, noting, "She's no fool but it's easy to deceive yourself when you're so committed to someone and believe he's committed to you." Indeed, Don Jr. and Guilfoyle (who started dating in 2018 and got engaged in 2020) continued to deny breakup rumors for several more months. It wasn't until December, when the Daily Mail spotted Don Jr. and Anderson having a romantic dinner and holding hands, that the engagement finally fell apart. Apparently, Don Jr. was spending most nights at Anderson's home rather than his and Guilfoyle's, and the article appeared to be the final nail in their coffin. The very next day, Page Six confirmed that Don Jr. and Guilfoyle had called off their engagement and Donald Trump announced that Guilfoyle would be the new U.S. ambassador to Greece.

Following confirmation of the breakup, Don Jr. had nothing but positive things to say about his ex-fiancee. "Kimberly [Guilfoyle] and I will never stop caring for each other and will always keep a special bond," he told Page Six. He also praised Guilfoyle's new gig in Greece as a U.S. ambassador. However, that very gig meant that his old and new flame were forced to spend quite a bit of time together leading up to Donald Trump's inauguration. Given Guilfoyle's role in Trump's administration, she was present at all of the various events in January 2025. Of course, Don Jr. was also in attendance and he chose to bring his new flame as his date. That meant that Guilfoyle and Bettina Anderson repeatedly crossed paths, including at a cryptocurrency ball on Friday, a candlelight dinner at the National Building Museum on Sunday, and at the actual inauguration ceremony on Monday where they were seen sitting on opposite sides of the Capitol Rotunda.

Despite the repeated run-ins, there appeared to be no drama, though. "Don Jr. and Kimberly, still have a cordial relationship," a source told the Daily Mail while another confirmed to People, "Kim saw Don with Bettina and it was all civil – no negativity." However, the insider added that Guilfoyle was hurt and did watch her ex and Anderson closely. "Kim is still very fond of Don and kept a watchful eye out," they mused.

Despite being caught by the tabloids and stepping out together on inauguration weekend, Don Jr. and Bettina Anderson didn't officially confirm their relationship until February 2025. That's when the duo went Instagram official while attending Super Bowl LIX in New Orleans, Louisiana. When Donald Trump became the first sitting president to watch the big game in person, he did so from the VIP box at Caesars Superdome and was accompanied by much of his family, including Don Jr. who made sure Bettina Anderson also had a seat.

During the event, Don Jr. posted Stories and photos to his Instagram, including snaps showing Anderson hanging out with him and three of the kids he shares with ex-wife Vanessa Trump: Donald, Spencer, and Chloe. Interestingly, the event was another occasion for Don Jr.'s love lives to collide, as Kimberly Guilfoyle was also present.

Don Jr.'s post came on the heels of a January Mediaite article in which seven unnamed Trump friends claimed that many in his inner circle were unhappy with Anderson's growing presence. "Individuals close to the president have expressed growing concerns about the potential liability posed by his son's new relationship," an anonymous source said. Another alleged, "Donald Trump does not approve of his son's association with Bettina."

Their relationship may have had a questionable start, but Bettina Anderson had no qualms about letting the world know just how strongly she feels about Don Jr. In March 2025, New York Magazine published a scathing profile about Don Jr. titled, "How the ultimate failson became an edgelord whisperer and bona fide power player." In one particularly headline-making passage, the outlet quoted a source as saying that the president's eldest son "is the most despised member of the family; he's an a**hole, a spoiled heir." The piece also went after Anderson, claiming she was simply dating Don Jr. to raise her own status, as she "used to look down on the Trumps."

Well, Anderson wasn't about to sit quietly by. However, rather than defending herself, she issued a passionate defense of Don Jr. in a series of Instagram Stories. "Rumors are started by haters, spread by fools, and accepted by idiots," she clapped back, per the New York Post. She also posted a screenshot of the quote criticizing Don Jr. and cheekily captioned it, "That's my guy!" Anderson then went on to praise her beau, writing, per the Daily Mail, that he was actually "the finest, loveliest, tenderest, and most beautiful and brilliant person I have ever known and even that is an understatement."

They initially tried to keep their connection under wraps, but Don Jr. and Bettina Anderson threw caution to the wind as they entered a new season of romance. Throughout the spring of 2025, the duo was repeatedly spotted acting giddy and packing on the PDA, starting at the 2025 amfAR Gala held in Palm Beach, Florida in March. The charitable evening, which raised millions for HIV research, was hosted by Coco Rocha and included a performance by Ricky Martin but the couple only had eyes for each other. Throughout the event, Anderson was snapped absolutely beaming as she sat next to her boyfriend and he draped his arm over her chair. In a separate pic shared by US Weekly, the socialite was seen smiling from ear to ear as she practically hung onto her beau.

They again put their romance on full display that April during the two-day LIV Golf Miami 2025 tournament. As the couple walked around the course at Trump National Doral, they were photographed laughing, hugging, and holding each other close. At one point, Anderson wrapped her arms around Don Jr. and appeared to adoringly squeeze him while he let out a big laugh.

Don Jr.'s inner circle reportedly isn't happy about his Bettina Anderson romance, but that hasn't stopped him from moving full steam ahead. Indeed, in February 2025, a source told People, "They're certainly going strong." The insider praised Anderson's sweet disposition and friendliness before enthusing, "I could easily see them going the distance." Similarly, another source told Us Weekly that Don Jr. was feeling "smitten" and was thoroughly impressed by Anderson's smarts while being attracted to her independence. "He wants a partner," they mused. "She doesn't need anything from him and just wants to be with him."

That March, Don Jr. took his Bettina relationship to the next level by presenting her to his family in a big way. As he shared on Instagram, he and his new love took three of his kids – Tristan, Spencer, and Chloe Trump – spearfishing for spring break. By the looks of it, Anderson got along splendidly well with Don Jr.'s kiddos as she posed with the family, a big smile on her face and her hands lovingly placed on Tristan's shoulders. Just a month later, reports surfaced that Don Jr.'s girlfriend was itching for a proposal. As one insider told the Daily Mail, "Bettina is ready for Don to lock things down and make it official with a ring."