Why US President Donald Trump might not attend his son's wedding: All about Donald Trump Jr's relationships

When you're the President of the United States, your family milestones don't just get handled in private—they get balanced against global warfare and intense media scrutiny. Case in point: Donald Trump might actually skip his oldest son's wedding this weekend.

When reporters point-blank asked him on May 21, 2026, if he’d be making the trip down to the Bahamas for Donald Trump Jr.’s wedding to Bettina Anderson, his answer was classic Trump: a mix of complaints about the "fake news" and a very real scheduling conflict.

“He’d like me to go. It’s going to be a small private affair. I’m gonna try and make it," Trump told the Oval Office press pool. "I said, ‘This is not good timing for me. I have a thing called Iran and other things.' That’s one I can’t win on. If I do attend, I get killed. If I don’t attend, I get killed… by the fake news, of course.”

With his usual dark humour, he highlighted a brutal PR trap. Going to a destination wedding while managing an active military conflict with Iran looks incredibly out of touch to voters. But skipping your eldest son's big day? That triggers a whole different wave of criticism about where your loyalties lie.

This wedding wasn't always supposed to be an under-the-radar island getaway. Initially, rumours swirled about a massive, high-profile celebration at the White House. But reality intervened.

With the war in Iran dragging on and domestic pressures mounting over rising living costs, throwing a lavish, politically supercharged party in Washington just wasn't a good look. So, Don Jr. and Bettina quietly pivoted. They swapped the grand political stage for an ultra-private, 50-guest ceremony on a small island in the Bahamas. It just shows how even the most powerful families in the world have to bend to the chaotic reality of global politics.

As if the geopolitical drama wasn't enough, the family is also dealing with a deeply personal shock. Just days before the wedding weekend, Don Jr.’s ex-wife and the mother of his five children, Vanessa Trump, took to Instagram to share some heavy news: she has been diagnosed with breast cancer.

Vanessa, who has been in a serious relationship with golf legend Tiger Woods since last year, confirmed she’s already undergone an initial medical procedure and is mapping out a treatment plan with her doctors. While she has managed to maintain an incredibly close co-parenting dynamic with Don Jr., this sudden health battle shifts the focus away from wedding glamour and toward real-life resilience and holding things together for the kids.

The romance between Don Jr. and Bettina Anderson has kept the tabloids pretty busy. The public first spotted them together back in August 2024, right around the time Don Jr. quietly ended his engagement to former Fox News host Kimberly Guilfoyle (who has since moved on to become the US Ambassador to Greece).

By early 2025, they were completely official, stepping out together at the inauguration and blending into the Palm Beach social loop. The relationship got the ultimate family stamp of approval in December 2025, when President Trump announced their engagement during a White House event, even joking that his usually talkative son was left "at a loss for words" when Bettina said yes.

Bettina Anderson isn't a political insider, but she’s certainly no stranger to high society.

The background: Born and raised in the elite circles of Palm Beach, Florida, she’s the daughter of prominent entrepreneur Harry Loy Anderson Jr.

The credentials: She graduated from Columbia University in 2009 with an art history degree.

The mission: Instead of just drifting through the socialite scene, she co-founded The Paradise Fund with her brothers—a highly active nonprofit focused on environmental conservation and sustainability, where she serves as executive director.

Her background in environmental activism and the arts presents a fascinating contrast to the hyper-political world she’s marrying into, adding some genuine depth to her public image.