When Billy Ray Cyrus and Elizabeth Hurley announced they were dating in an Easter-themed Instagram post, it felt like two very different worlds colliding.
It wasn’t just seeing Hurley seemingly out of her element in plaid flannel and a cowboy hat on a farm when her feed is typically bikini hot shots and red-carpet glam pics. Or seeing Cyrus, who has had family members concerned for his well-being, playfully sporting bunny ears while going in for a kiss. On paper, the British actress-model and the Nashville-area-based country singer, who has divorced twice since 2022, seem like an unusual match.
We weren’t the only ones with that thought. “Who else totally did not have this on their 2025 bingo card?” one person commented on the couple’s post. Others wrote, “Is today April 1st?” and “THAT is bizarre.”
Even other famous people were thrown by the news. Little House on the Prairie actress Melissa Gilbert commented, “Wait…what?” For what it’s worth, Hurley’s adult son, Damian Hurley, gave his OK via emoji, writing: “🥳♥️.”
As odd a pairing as they may seem, there is a backstory for the new couple. Hurley and Miley Cyrus’s dad costarred in the 2022 movie Christmas in Paradise, so they’ve known each other for at least two and a half years. According to People, they’ve been “seeing each other romantically for a little bit” and she visited him over Easter.
Cyrus and Hurley join a long list of other unlikely celebrity pairings. The idea that “opposites attract” is as old as time and doesn’t just fuel real-life relationships, but is a long-running theme in movies, on TV shows and in songs.
The coupling that ‘caught everyone by surprise’
“This is not a pairing I, nor the public, could have expected,” celebrity matchmaker and relationship expert Carmelia Ray told Yahoo Entertainment. “Based on the reaction from other celebs and their fans, it caught everyone by surprise.”
So what makes a good couple in the first place? It’s “two people who align with their attitude, values, lifestyle, goals and key core compatibility,” she said. “They are emotionally mature, have high EQ (emotional quotient) and understand their attachment styles.”
Ray thinks that “aesthetically they seem like a good match,” but more than that, they’re also within a “reasonable age range.” Hurley is 59 and Cyrus is 63, “which is uncommon in many celebrity relationships,” she said, pointing out that Brad Pitt, Madonna and Cher all have much younger partners.
Hurley and Cyrus met while filming 2022’s Christmas in Paradise in the Caribbean. (Lionsgate)
Alessandra Conti, a matchmaker and dating coach, also applauds the “age-appropriate match,” especially for Cyrus, who’s coming off a bitter divorce from singer Firerose, 36, after less than a year of marriage. Cyrus’s 28-year marriage to Tish Cyrus, 57, ended in 2022, and he was married to Cindy Smith from 1986 to 1991.
“The fact that Billy Ray had a marriage that lasted 28 years with a woman who was age-appropriate versus seven months with a woman who was half his age is telling in terms of who he is going to have compatibility with long term and bodes well for his new relationship with Elizabeth,” Conti told Yahoo.
Conti thinks that the pairing “may be better for Billy Ray than it is for Elizabeth” on the heels of Cyrus’s son Trace saying he and his siblings were “genuinely worried” that they may “lose” their dad “far too soon” due to unspecified struggles. Hurley “lives an incredibly healthy lifestyle, and although she isn’t technically sober, she says that she barely drinks, doesn’t smoke, doesn’t eat processed foods or sweets and has tons of vegetables.”
While Hurley may be able to help Cyrus get back on track, isn’t jumping into a new romance with someone who has had back-to-back divorces red flag city?
“Two divorces in two years is a pattern that needs serious attention and consideration, and is at best a bright yellow flag and at worst a big red flag,” Conti said. “If Elizabeth was my client, I would coach her to guard her heart and proceed with extreme caution.”
Ray doesn’t see divorce as “an immediate red flag” if Cyrus and Hurley do the work and establish a relationship of truth and transparency.
“At the end of the day, love isn’t about being perfect — it’s about finding the right fit,” Ray said. “If they’re happy together, I’m rooting for them to prove the doubters wrong. My advice? Focus on building trust, learn from the past, and keep their connection and communication front and center. The world might be watching, but they should let their hearts lead the way.”
After all, Hurley’s experienced some relationship woes too. She’s divorced from Arun Nayar, dealt with Hugh Grant’s infamous scandal while they were together in the ’90s and had a very public battle with ex Steve Bing over Damian’s paternity.
Hurley with her son, Damian. (Thomas Banneyer/picture alliance via Getty Images)
“I am a big believer that growth is very real, especially as life happens,” said Conti. Hurley “has experienced motherhood, divorce, the death of her ex-fiancé [Shane Warne]. This woman has been through it and has come out stronger than ever.”
And while Hurley seemed, at first glance, like a fish out of water on Cyrus’s farm, for years she ran her own 400-acre organic farm in Gloucestershire, England. She already owns flannel shirts, wellies and cowboy hats — and has her own chickens. We’d wager to say that Cyrus finding his way in her world — the nonstop red carpets and beach trips — may be the more challenging fit. Not to mention having the Atlantic Ocean between them.
Why do people even care about Hurley and Cyrus’s romance and compatibility?
That brings us to why we care about two famous people — who most of us don’t know — getting together in the first place. It’s deeply ingrained in human behavior, whether the person we’re talking about is famous or not.
“Why do young people in high school get so invested in who everyone is dating? Why do we gossip about others in this way? It’s a fixture, particularly of adolescence, to focus on these kinds of things,” Empire State University psychology professor Gayle Stever told Yahoo. “The focus on media celebrities and their relationships is similar to those same behaviors that we engage in with people in our own day-to-day lives. If two people at work are dating, doesn’t everyone whisper about that?”
Media in general — and now social media — has “widened the circle of people who are known to us,” even if we don’t know them directly.
“Just as we engage in gossip about those we know in a face-to-face context, people love to gossip about people who are in that extended social realm that we call ‘media,’” said Stever, who authored the book The Psychology of Celebrity. “Media has widened our circle of acquaintances from the social into the parasocial realm, and the same behaviors we exhibit in the social areas of our lives are also a part of the mediated parasocial parts of life. Everyone has parasocial relationships, [which are] simply defined as knowing someone who doesn’t know you back.”
OMG’ing over Hurley and Cyrus on social media “is an extension of that.”
