Kaitlan Collins' Rumored Boyfriend Has A Sketchy Age-Gap Relationship Under His Belt

CNN's Kaitlan Collins recently made news when Donald Trump escalated their feud with a gross eight-word attack, infamously telling the journalist, "I don't think I've ever seen you smile" (via YouTube). Yet she also had folks buzzing for another reason just days prior. Collins hit the 2026 Grammys red carpet with a man on her arm. And, perhaps to Trump's surprise, she and her possible new beau were all smiles. This sparked questions about the mystery man's identity. Unfortunately, as more info about Collins' date was uncovered, so was one strange detail about his past. 

The man Collins hit the red carpet with was none other than photographer Emilio Madrid. Madrid's photography portfolio is chock-full of high-profile celebs. And according to the Daily Mail, he calls himself a "political and portrait junkie." So, it seems he might be a perfect match for a famous White House correspondent. Yet, one star who Madrid photographed in the past is giving people pause. Back in 2019, the now 30-year-old Madrid was 24 when he publicly confirmed that he was in a relationship with freshly 18-year-old Broadway actor Sophia Anne Caruso. The pair met when Madrid was a photographer for Broadway.com, and Madrid was the photographer on multiple different photoshoots featuring Caruso before she turned 18.

While there are some questionable things about Emilio Madrid's relationship with Sophia Anne Caruso, he didn't seem shy about flaunting their romance online. He shared multiple Instagram posts about his then-girlfriend, which are still up on his grid to this day. In 2020, he shared a photo of him and Caruso in front of his house and called her "the prettiest thing in this photo" in the caption. The following year, he shared a mirror selfie of the pair, which attracted comments like, "Awww you guys are so cute."

The age-gap relationship is being called into question now that Madrid is rumored to be dating Kaitlan Collins, who is three years his senior. Yet, an insider told the Daily Mail that these romance rumors are simply rumors. While Collins only shared photos on Instagram showing her alone and her posing with Madrid at the Grammys, the source claims that the pair was actually at the event with a group, and the photo choices were nothing worth reading into. This gossip comes nearly a year after a source told National Enquirer, "Kaitlan's not just looking for love," adding, "She's also looking for someone who can keep up with [her] career and help her navigate the social and political circles she thrives in." So, here's hoping that a scandal-free flame who's Collins' perfect fit is just around the corner.