Donald Trump Jr. recently announced his engagement to his socialite girlfriend, Bettina Anderson. As the pair takes a step forward, both of them are trying their best to keep Don Jr.’s relationship history in the past. However, his father, Donald Trump, is not so willing. Yes, he did congratulate his daughter-in-law-to-be, but his message did not have the usual celebratory sentiments; it was quite cryptic.
The POTUS met Anderson during the December 15 White House Christmas reception. He kissed his son’s new fiancée on the cheek and delivered a short but not-so-sweet message. “Good luck,” Trump seemed to have said to Bettina. Now, you might ask, why is it ominous? Well, observers have suggested this sounded more like a warning than a congratulatory remark.
🚨 BREAKING: President Trump just announced from the White House that Donald Trump Jr. and Bettina Anderson are officially engaged and planning to get married.
Yes, this was announced at the White House.
America, 2025. pic.twitter.com/ptpOjIRBbu
— Brian Allen (@allenanalysis) December 16, 2025
If Trump wanted to just shortly congratulate Anderson, he could have chosen to say “congrats,” or something like “welcome to the family.” However, the POTUS’s choice of words for his daughter-in-law-to-be has surely raised some eyebrows. Some even questioned if it was an intentional warning, given Don Jr.’s track record of failed relationships. Is Trump trying to say that their engagement would not last?
It is possible that the Republican POTUS was trying to remind her of how last year, around this time, his son broke off another engagement. For context, last December, Donald Trump Jr. announced that he had split from Kimberly Guilfoyle. The couple began dating in 2018. Two years later, they got engaged. After the split, he wasted no time in making things official with Bettina Anderson.
Not even weeks had passed since he announced his split from Guilfoyle, Don Jr. was already celebrating Christmas with Anderson at Mar-a-Lago. Even before the former couple broke up, there were rumors of Don Jr. having an affair with Anderson. The leaked photo from Christmas 2024 only solidified that chatter.
It appears Don Jr has split from his fiancée Kimberly Guilfoyle, and moved on with his new love socialite Bettina Anderson. pic.twitter.com/PiFpMTImSK
— Mike Sington (@MikeSington) December 10, 2024
However, this is not the first time Donald Trump’s son has been criticized for allegedly cheating on his partners. Rumor has it that he even cheated on his first wife, Vanessa Trump, while she was pregnant with his child. They ended their marriage in 2019, and a year later, Don Jr. made things serious with Kimberly.
Based on his track record, experts predict that there are serious signs that his relationship with Bettina Anderson could face some issues, even if the pair had already gotten engaged. So, the big question now is, has Don Jr. put his alleged adulterous behavior in the past, or is Trump’s “Good Luck” a warning message to Bettina?
