Revisiting Madelyn Cline’s Relationship History Now That She’s (Reportedly) Got a New Man

It seems like Madelyn Cline is everywhere you look these days. Between The Comeback King, season 5 of Outer Banks, and Sabrina Carpenter’s “House Tour” music video, the former Cosmo cover girl is booked and busy—but somehow, she still makes time for fueling romance rumors.

So…who is Madelyn Cline dating these days? According to TMZ, Madelyn split from influencer Henry Smith after four months of dating...and according to Deuxmoi, she may have moved on with a mysterious real estate executive. Curious who else she’s dated (or, at least, reportedly dated) in the past? I’ve got you covered.

Hi, remember this?? Madelyn and her Outer Banks costar Chase Stokes started dating in April 2020, and they hard-launched their relationship a few months later with a cute IG post.

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Sadly, multiple sources confirmed their split in November 2021. “Madelyn and Chase are no longer together,” one source claimed to People. “They were trying to work things out privately but broke up a couple of months ago.”

Dating rumors about Madelyn and Ross Butler first started circulating in September 2021, when the two were spotted dancing together at a restaurant in Milan.

However, Ross later shut down the rumors, telling TMZ that Madelyn was “just a friend.” Per Ross: “I dance with a lot of people.” Case closed!

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Madelyn was first photographed with musician Jackson Guthy in June 2022—but it wasn’t until December of that year that Madelyn dropped the word “boyfriend” while chatting with The Cut. Later, in March 2023, Madelyn posted Jackson to her Stories, finally going public with the relationship.

After just about a year of dating, Jackson and Madelyn reportedly went their separate ways in July 2023.

News of Madelyn and Pete Davidson’s relationship first broke in September 2023. “Pete and Madelyn are dating,” a source told Us Weekly at the time. “They spent the night together at the Beverly Hills Hotel and then had breakfast together there the next morning.”

The pair went strong for just about a year before things fizzled out in July 2024. According to a source for The Sun, “They ended things fairly recently, and I understand it was amicable.”

Madelyn was initially linked to Zack Bia in December 2021, not long after her breakup with Chase. Just a month later, during an appearance on the BFFs With Dave Portnoy and Josh Richards podcast, the DJ set the record straight on where he and Madelyn stood. “We never officially started dating and probably will never officially stop because we are just hanging out,” he explained. “We are enjoying it and not even thinking about what it is.”

The two sparked dating rumors a second time in June 2025, which is when a fan captured them looking cozy at Audemars Piguet’s 150th anniversary celebration. Pls see for yourself:

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But by the following month, Madelyn made clear during an interview with Allure that she was “single and not quite worried about settling down yet,” so I guess that’s that on that.

In September, Madelyn sparked romance rumors with actual royalty when a Deuxmoi tipster snapped her with the prince, writing, “Just saw Madelyn Cline with Prince of Greece on Madison Ave. They were like giggling and in sweats.”

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However, the rumors fizzled out just about as quickly as they began. Moving on!

Not long after Madelyn attended a live show for Brooke and Connor Make a Podcast with influencer Henry Smith (as spotted by a Deuxmoi tipster), a source for Us Weekly confirmed that the two were officially dating.

The couple went on to date for about four months, posting several TikToks together like this gem:

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But then, in June 2026, TMZ reported that the pair had called it quits. It was fun while it lasted!

Madelyn’s latest (reported) beau? That would be real estate executive Michael Reyes, who was spotted with Madelyn enjoying “a dinner of mussels and white wine at El Cava in Studio City,” per a Deuxmoi tipster. Little is known about Michael other than the fact that he has a lot of celeb connections (yep, that’s him with Rob Lowe’s son John Owen Lowe, above!), so chances are they met through mutual friends.

More on this budding romance as I have it!