Donald Trump Jr. was married to Vanessa Trump (née Haydon), a model, from 2005 until their divorce in 2018. They share five children together. He has not remarried as of late 2025, though he was previously engaged to Kimberly Guilfoyle (split around 2024) and recently announced his engagement to Bettina Anderson in December 2025.

Marriage Timeline

Donald Trump Jr. met Vanessa Haydon in the early 2000s at a fashion event arranged through his father. They wed at Mar-a-Lago in 2005 and separated amicably in 2018 amid reports of his alleged affair with Aubrey O'Day, finalizing the divorce soon after.

Key Milestones:

  • 2005 : Married Vanessa Haydon.
  • 2009-2018 : Parents to Kai, Donald III, Tristan, Spencer, and Chloe.
  • 2018 : Vanessa files for divorce; joint custody granted.

Post-Divorce Relationships

After the split, Trump Jr. dated Fox News host Kimberly Guilfoyle starting in 2018, getting engaged in 2020. The relationship ended quietly by late 2024, coinciding with rumors of his new romance.

He began dating socialite Bettina Anderson around mid-2024, spotted together in Palm Beach. President Donald Trump announced their engagement at a White House holiday event on December 15, 2025—no wedding date yet.

Family and Public Impact

The Trumps emphasized co-parenting post-divorce, with Vanessa focusing on raising their kids out of the spotlight. Recent engagement news trended on forums like X and Reddit, blending celebrity gossip with political chatter amid Trump family updates.

Public Views:

  • Supporters praise his family-man image.
  • Critics highlight tabloid drama from past affairs.

TL;DR : Sole marriage was to Vanessa Trump (2005-2018); now engaged to Bettina Anderson.

Information gathered from public forums or data available on the internet and portrayed here.