Donald Trump Jr. was spotted out with Florida socialite Bettina Anderson on Monday, December 9, leaving many wondering about his relationship status with longtime fiancée Kimberly Guilfoyle. The 46-year-old was seen holding hands with Anderson during a nighttime stroll in Palm Beach, Florida. According to Daily Mail, they were celebrating Anderson's birthday and spent nearly two hours at the popular downtown restaurant Buccan.

Uncertainty in Trump Jr.'s Relationship

Although the eldest son of President-elect Donald Trump has not publicly announced the end of his relationship with Guilfoyle, who is 55 years old, sources told PEOPLE in September that they had been spending a lot of time apart. At that time, one source described Trump Jr. as more independent, coming and going as he pleased and quietly seeing Anderson. PEOPLE tried to reach Trump Jr., Anderson, and Guilfoyle for comment about the latest relationship reports.

Early Beginnings and Engagement

Donald Trump Jr. and Kimberly Guilfoyle first started dating in early 2018 after knowing each other for years. They got engaged in 2020 but did not publicly reveal the news until two years later. The couple was frequently seen together, whether on the campaign trail or in Jupiter, Florida, where they live with their blended family. Guilfoyle, who was previously married to California Gov. Gavin Newsom, shared during a 2021 appearance on Successful Philanthropy, "We really are a team, we support each other, we're best friends. We have great conversations and a lot of laughs together. It's great we have such a strong relationship. It's never wavered and I really feel blessed to be a part of it."

Guilfoyle's Perspective on Their Relationship

In an interview with Metropolitan Palm Beach magazine in 2022, Guilfoyle elaborated on their relationship, saying, "I love taking care of Don, the way I saw my mother lovingly take care of my father. I go out of my way to make sure he has everything he needs – making coffee in the morning, cooking our favorite meals, doing our families' laundry, and caring for our home."Donald Trump and Kimberly Guilfoyle.Kimberly Guilfoyle InstagramNever miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.