Kaitlan Collins' Mystery Man Emilio Madrid's Past Exposed — Including His Questionable 'Love Affair With a Young Drama Student'

Kaitlan Collins' rumored new boyfriend, Emilio Madrid, has a questionable past when it comes to his dating history, RadarOnline.com can reveal.

The CNN host, 33, made her PDA-filled red carpet debut with the celebrity portrait photographer at Clive Davis' pre-Grammys party. The following night, the duo attended the Grammys ceremony as each other's dates.

Madrid previously dated Broadway actress Sophia Anne Caruso, despite a six-year age difference and a timeline of stepping out as a couple when she was barely an adult.

The duo went public with their relationship in September 2019, three months after she turned 18 and he was 24 at the time. They met when she was pursuing her acting career, and he was a staff photographer at Broadway.com.

The Daily Mail reported Madrid photographed Caruso, 24, for several fashion shoots, including the brand Celine, when she was a 17-year-old. The duo made their red carpet debut at Celine's Paris Fashion Week show.

The outlet reported that the Ruthless! The Musical star initially "appeared open to speaking" but immediately shut down their conversation with a "no comment" as soon as her youthful romance with Madrid was brought up.

Caruso was a regular presence on Madrid's Instagram page throughout their relationship, and his personal photos with her stood out since his account is devoted to portraits of the stars that he took.

In September 2020, Madrid announced he was a "Homeowner" with a snapshot of the pair sitting on the steps of his new house in the Catskills.

He added of the loved-up picture, "Me, not her, Sophia simply does the interior design, and is the prettiest thing in this photo. And yes, you can all come visit someday."

Madrid shared a series of portraits of his then-girlfriend in July 2021, including ones of her posing with animals and another in a red and white striped swimsuit, writing, "Happy birthday, best friend."

The former couple was still going strong as of November 2021, when Madrid posted a selfie of the two with Caruso's arms lovingly locked around his waist.

"This photo reveals that I put AirTags on my cameras," the caption read, and the snapshot, like all of the others with Caruso, is still on his Instagram page.

Madrid shared October 2022 behind-the-scenes photos of Caruso celebrating at the after-party following the Los Angeles premiere of her fantasy film The School for Good and Evil.

He told followers to "fire up your Netflix" and watch the movie, as a smiling Caruso posed with her director, Paul Feig. Another Polaroid showed Madrid, looking dapper in a double-breasted ivory suit, and Feig posing together.

Collins sparked romance rumors with Madrid when they posed with their arms around each other on the red carpet at Davis' annual bash on January 31.

He had his arm adoringly around the CNN White House senior correspondent the following day as they posed on the rooftop of their hotel before heading to the Grammys. Collins shared the snapshot with her 1.4 million Instagram followers.

Madrid returned the favor, including several Instagram Stories alongside the political bulldog, where the pair looked so glam and dressed to the nines during their outings on Grammys weekend.

The red carpet PDA was rare for Collins, who is notorious for keeping her private life out of the spotlight.