Who Kimberly Guilfoyle Should Date In 2025 According To Our Matchmaker

After being engaged for four years, Kimberly Guilfoyle and Donald Trump Jr. have split up, and it may have been messier than it seems. While we may never know what exactly went on between the two of them as their relationship came to an end, we do know that Don Jr. has moved on with Bettina Anderson, who'd long been rumored to be his mistress. Now, Guilfoyle might also be on the lookout for a new romantic partner. The List spoke with Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, about Guilfoyle and the type of man she might match with in 2025. And her pick totally makes sense.

"I do think maybe a Greek businessman who is a little more worldly will be a match for her," Trombetti told us. "I would bet money that will be it. There won't be much media attention, and it will provide some privacy and space for things to develop a little more naturally in a relationship."

Guilfoyle's likely to have plenty of opportunities to meet Greek businessmen in 2025 since Donald Trump has named her as his choice for ambassador to Greece. However, she will have to get Senate approval before she can take the job (and possibly meet Mr. Right). It could be a Jackie Kennedy and Aristotle Onassis kind of moment for Guilfoyle; after all, when Guilfoyle was married to Gavin Newsom, they got compared to the Kennedys.

Kimberly Guilfoyle might want to hold out before looking to start a new relationship at her home in Florida before her new position is confirmed and she has to move to Greece. Long-distance relationships don't always last, and they can be hard to cultivate from across an ocean. "Her role as ambassador would definitely impact any stateside relationship unless they work remotely," Susan Trombetti said. "Some couples are used to reconnecting after long times apart, but we all know being near each other is what's best for any relationship to survive and develop at a natural pace. That's why I think a Greek businessman would be good for her."

It might be that anyone in the U.S. who is looking to start a relationship with Guilfoyle would be doing so for the wrong reasons, considering her ties to Donald Trump and the Republican party; though she's no longer with Don Jr., she's close enough to the Trump administration to be appointed ambassador even after the breakup. "Men will be using her to get to Trump anyway," Trombetti theorized, "so she should wait until she isn't vulnerable and can pick a better match." Looking for someone in another country could help distance her from being used for her potential connections to the presidency.

Even though Susan Trombetti doesn't really see all that many great options for Kimberly Guilfoyle in the U.S. at the moment, that might be a good thing. "At this point, whether there are eligible bachelors in her social circle, I think she needs to take a break and reassess her relationship failures and not run off so quickly." Before her engagement to Donald Trump Jr. and after her marriage to Gavin Newsom, Guilfoyle was married to Eric Villency from 2006 to 2009.

Time could be just what Guilfoyle really needs at this point. She was with Don Jr. for years, since 2018, and ending a relationship, even if it's amicable, is often hard, and getting over a breakup can take time. So, instead of jumping into a new relationship (like Don Jr. seems to have done), she might be better off staying single for a bit. "I don't think she should be considering a relationship until she has processed her breakup and taken time to reflect." 

Then again, love is love, and you never know when and where you might find it. As Trombetti told us, "Sometimes, something ignites and just feels right."