Don Jr. Can't Shake His Shady Dating Reputation With Bettina Anderson Proposal

Donald Trump Jr. is repeating history with his proposal to Bettina Anderson. He was married to his ex-wife Vanessa Trump for 12 years. After they called it quits in 2018, he started dating Kimberly Guilfoyle that same year. Two years later he popped the question, and in December 2024, they broke up. Rather than taking his time to process his breakup with Guilfoyle, Don Jr. made things official with Anderson almost right away. Suffice it to say, Donald Trump's oldest son doesn't typically take things slow in relationships, and this has folks seeing plenty of signs that he and Anderson will never last. 

It's been just a year since Don Jr. and Guilfoyle announced their breakup before they ever made it down the aisle, and he's already popped the question to his latest bride-to-be. At a December 15 holiday party at the White House, Don Jr. took the podium to announce that he is a fiancé once again. With a formal announcement like this one, the happy couple was likely expecting plenty of congratulations and well wishes. When a clip of the big moment landed on X, (formerly Twitter), however, many netizens were more focused on the red flags in Don Jr.'s past than the wedding bells in his future.

"Is this like his 6th wife?" one person commented on the clip of Donald Trump Jr. and Bettina Anderson announcing their engagement on X. In reality, Don Jr. has only been married once, but he wastes no time hopping from one partner to the next. And, folks have taken note. "I thought marriage was sacred, is this his second or third?" another commenter asked. "How many times has Don Jr announced that this one is the love of [his] life?" another X user added with a laughing emoji. Another commenter summed it up well, simply writing, "Ugh, bad batting average." 

And, if there was any question as to whether this relationship was moving at an unusually swift pace, there was evidence that many people didn't even realize Don Jr. had broken up with his ex. Yikes. "I thought he was already married," one commenter wrote. "Oh ! Wait ! What happened to Kimberly?" asked another.

People want different things out of their relationships. Yet, there are likely very few people who want news of their engagement to be met with confusion because people thought your hubby-to-be was still engaged to his ex. Still, hopefully Anderson can take heart in the comments from folks who are wishing the couple well. Only time will tell if this romance is as doomed as the rest of the commenters seem to think it is.