The Australian native, 22, fueled breakup rumors after he was spotted spending time with a tall blonde over the weekend who was not Cyrus, 27.
According to TMZ, Simpson stepped out on Saturday in New York City with Playboy model Jordy Murray, who was dubbed the magazine's December 2019 playmate. Simpson's questionable outing came after Cyrus released a somber song about being alone for the holidays.
Simpson and Murray were both bundled in winter attire as they chatted on the city streets, according to photos obtained by the outlet.
"A sad Christmas song I wrote a few years back right before the holidays. Was feeling like s--t cause I couldn't be with the one I loved. Even with a house full of family and friends I still felt alone," Cyrus wrote on Instagram. "In ways that still feels relevant and someone reading this right now could possibly relate! If you feel lonely this season just know YOU ARE COMPLETELY MADE OF MAGIC! You are as special as a snowflake, beautifully unique and I hope inside your soul feels light, hope, peace and joy knowing how singularly amazing YOU are! Love always wins!"
"PS @waynecoyne5 & @stevendrozd are so bad ass for helping me put this together so f--kin fast so I could share w my fans by Christmas! Recorded at my little garage studio in LA, I wrote the song driving there from Malibu! @vijatm is always the best at turning my crazy idea into reality and created this set up so I could shoot a cover the same night! @bradleykennetheyewear," the pop star continued.
Cyrus and Liam Hemsworth, 29, announced their separation in August after eight months of marriage. Hours prior, photos surfaced of the "We Can't Stop" singer kissing Brody Jenner's ex, Kaitlynn Carter, while vacationing in Italy.
Cyrus and Carter briefly dated until Hemsworth's ex moved on with Simpson. Earlier this month, Simpson spoke to E! News and hinted at the singers possibly collaborating on a track together.
Meanwhile, Hemsworth was recently spotted in Australia, where he appeared to introduce his parents to rumored new girlfriend, model Gabriella Brooks.
Cyrus continues to appear bitter about her divorce, as she recently joked to a fan who was vocal about tying the knot with her that it "probably won't last long."