Donald Trump Jr. began dating former Fox News host Kimberly Guilfoyle after his divorce from Vanessa Trump, and more recently he has been linked to (and then engaged to) socialite Bettina Anderson.

Quick Scoop: Who Did Donald Trump Jr. Date After His Divorce?

Focus keyword: who did donald trump jr date after his divorce

When Donald Trump Jr. and Vanessa Trump finalized their divorce (they separated in 2018 and finalized things around 2019), his romantic life moved back into the spotlight. Here’s the post‑divorce sequence that’s most consistently reported in public sources.

Immediate Post‑Divorce Relationship: Kimberly Guilfoyle

Soon after his split from Vanessa, Donald Trump Jr. started dating Kimberly Guilfoyle, a former Fox News personality and prominent Republican figure.

  • They reportedly began dating in 2018, right after his divorce from Vanessa Trump was finalized.
  • The relationship was very public: she appeared with him at campaign events and Republican gatherings.
  • Multiple outlets report that they became engaged; they bought a home together in 2021 and were described as fiancĂ©s through the early 2020s.

So, if you’re asking “who did he date right after his divorce?” the answer most sources agree on is Kimberly Guilfoyle.

Later Relationship: Bettina Anderson

After several years with Guilfoyle, reports emerged that the engagement had ended and that Trump Jr. had moved on with socialite Bettina Anderson.

  • By late 2024, gossip and news outlets were reporting he had “called off” his engagement to Guilfoyle and was now dating Anderson, a Palm Beach/Palm Springs–connected socialite.
  • He was photographed walking hand‑in‑hand with her and attending high‑profile Trump family events, including New Year’s Eve at Mar‑a‑Lago and Inauguration Day in Washington, D.C.
  • Coverage in 2025 and early 2026 notes that they dated for about a year before getting engaged in December 2025, with some reports indicating they later married over Memorial Day weekend 2026.

This means that after his divorce and long relationship with Guilfoyle, he entered a new relationship (and later engagement) with Bettina Anderson.

Mini Timeline Table (HTML)

Below is a simple HTML table summarizing the key post‑divorce relationships:

html

<table>
  <thead>
    <tr>
      <th>Period (approx.)</th>
      <th>Partner</th>
      <th>How They Were Described</th>
      <th>Key Notes</th>
    </tr>
  </thead>
  <tbody>
    <tr>
      <td>2018 – 2024</td>
      <td>Kimberly Guilfoyle[web:15][web:20]</td>
      <td>Girlfriend, later fiancée[web:15][web:20]</td>
      <td>Started dating after his divorce from Vanessa; high‑profile public couple; engagement widely reported.[web:15][web:20]</td>
    </tr>
    <tr>
      <td>Late 2024 – Dec 2025</td>
      <td>Bettina Anderson[web:10][web:15][web:12]</td>
      <td>Girlfriend[web:10][web:12]</td>
      <td>Spotted hand‑in‑hand and at various Trump family events; described as a socialite from Palm Beach/Palm Springs.[web:10][web:15]</td>
    </tr>
    <tr>
      <td>Dec 2025 – 2026</td>
      <td>Bettina Anderson[web:12][web:19]</td>
      <td>Fiancée, later wife[web:12][web:19]</td>
      <td>Engagement announced December 2025; reports say they married in the Bahamas over Memorial Day weekend 2026.[web:19]</td>
    </tr>
  </tbody>
</table>

Multiple Viewpoints & Gossip Caveats

Because this is celebrity‑relationship territory, there are a few important caveats:

  1. Official vs. tabloid narratives
    • Mainstream outlets (like Business Insider and regional papers) focus on confirmed, on‑the‑record relationships: Vanessa (ex‑wife), Kimberly Guilfoyle (long‑term partner/fiancĂ©e), then Bettina Anderson (girlfriend → fiancĂ©e → wife).
 * Gossip columns and forums sometimes speculate about other flings or overlaps, but those are rarely confirmed and can be unreliable.
  1. Timing overlaps and speculation
    • Some reports suggest Trump Jr. was seen with Bettina Anderson before an official confirmation of his split from Guilfoyle, which fuels online debate about overlap.
 * However, both he and Guilfoyle have kept details of their breakup largely private, so exact timelines can differ slightly between sources.
  1. Current status (as of mid‑2026)
    • Most recent timelines indicate Trump Jr. and Bettina Anderson are married, following their engagement in late 2025 and a reported wedding in the Bahamas in May 2026.

Short TL;DR at the Bottom

  • Right after his divorce from Vanessa Trump: Donald Trump Jr. dated Kimberly Guilfoyle , and they were engaged for several years.
  • Later on: He ended things with Guilfoyle and began dating Bettina Anderson , a socialite he later got engaged to in December 2025 and reportedly married in 2026.

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