Sounds Like Don Jr. Had an Awkward Weekend

Photo-Illustration: by The Cut; Photos: Getty Images

You would think all Trump’s fans — particularly his blood relatives — would be having a blast the weekend of his inauguration, but maybe not Donald Trump Jr. Instead, Trump’s oldest son and his girlfriend Bettina Anderson seem to have spent the weekend avoiding awkward run-ins with his ex-fiancée Kimberly Guilfoyle.

Until recently, Don Jr. was engaged to Guilfoyle, a former Fox News correspondent, but they broke things off after months of rumors — and sightings of Don Jr. on a flirty outing with Florida socialite Bettina Anderson. Now that they’re officially over, Guilfoyle has seemingly been appointed ambassador to Greece so that Don Jr. and Anderson can live out loud as a couple. But not so soon — during the inauguration weekend, which was Anderson’s first time attending public political events, Guilfoyle was still lurking about, forcing all three of them to hang out in close proximity. On Friday, Don Jr. brought Anderson to a cryptocurrency ball where Guilfoyle was also in attendance, and they were also all photographed (separately, thank God) at a candlelight dinner at the National Building Museum on Sunday.

Further fueling the tension: Though Don Jr. may have picked Anderson thinking she would impress his dad more than Guilfoyle did, rumors are flying that Trump actually hates her. According to Mediaite, Trump’s inner circle is worried about Anderson’s reputation for partying and dating wealthy men, and Trump himself “does not approve of his son’s association with Bettina.”

By Monday, neither woman was sitting anywhere near the Trump family during the inauguration ceremony — even though Anderson seems to have been getting her “Inauguration Glam” done early Monday morning, according to an Instagram Story posted by a woman who seems to be doing her makeup. Sounds like a tense weekend was had by all.

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