New reports indicate that Donald Trump Jr. has announced his engagement to socialite Bettina Anderson, following a year-long relationship and a recent breakup with former fiancée Kimberly Guilfoyle.

The news comes after Donald Trump Jr., the eldest son of President Donald Trump, began dating Anderson last year, coinciding with the end of his bond with Guilfoyle. Sources confirm that Donald Trump Jr. proposed to Anderson, who has accepted his proposal.

Guilfoyle and Donald Trump Jr. started dating in 2018 before getting engaged in 2020. News that they called it quits became public in December 2024, with reports indicating the couple separated ahead of the election but kept the timing quiet to avoid overshadowing Donald Trump Jr.’s father’s campaign. According to an insider, Donald Trump Jr. initiated the split, stating, “Kimberly and I will never stop caring for each other and will always keep a special bond.” He also expressed satisfaction that Donald Trump had appointed Guilfoyle as U.S. ambassador to Greece.

While public statements from Donald Trump Jr. praised Guilfoyle, private concerns about her style were reportedly addressed, with sources noting she was told to move away from “tacky” clothing and adopt more casual attire. Days before the breakup was confirmed, photographs surfaced of Donald Trump Jr. holding hands with Anderson, fueling speculation about his new relationship.

An insider explained that Donald Trump Jr. has always sought approval from his father, and Anderson—described as a model in Palm Beach social circles—was seen as a better match for him than Guilfoyle. This development follows months of discussions where Donald Trump Jr. reportedly criticized Guilfoyle’s professional attire, stating she “never looks relaxed or casual” in high heels and tight dresses.