Scheana Shay emotionally recalls two painfully awkward encounters with ex John Mayer at ChainFEST years after their brief 2008 romance, revealing how a hug, a rejected photo, and a cold handshake reopened old feelings and left her reflecting on an unresolved chapter of her past.

Reality star Scheana Shay is no stranger to headline-making moments, but her latest revelation in her newly released memoir My Good Side has reignited interest in one of her most surprising past relationships: her brief romance with Grammy-winning musician John Mayer.

More than a decade after their casual fling made quiet waves in the celebrity gossip circuit, Shay has offered an unfiltered account of what happened when she unexpectedly crossed paths with Mayer not once, but twice — and both times ended in painfully awkward interactions.

The Vanderpump Rules alum, 40, first encountered Mayer, now 47, at ChainFEST, a gourmet food festival held annually in Los Angeles, in 2023.

Shay told PEOPLE in a recent interview that the reunion was anything but smooth. “I saw him, and I awkwardly gave him a hug,” she recalled.

“I was like, ‘Hey,’ and then made a joke like, ‘Oh, we should get a photo.’ And he was like, ‘No.’ And I was like, ‘I was kind of kidding.’ But yeah, that was awkward.”

ChainFEST, known for bringing together foodies, influencers, and A-list guests, seemed an unlikely stage for old romantic drama, but for Shay and Mayer, it became the setting for a moment steeped in discomfort and mixed signals.

The two had not seen each other in years since their quiet six-month fling in 2008 — a relationship that began shortly after Mayer’s high-profile breakup with Jennifer Aniston.

Shay, who was working at Mayer’s birthday party that year, writes in her memoir that the connection began casually but took unexpected turns, including what she describes as a “throuple” dynamic involving herself, Mayer, and her then-roommate Stacie Adams — also known to The Hills fans as “Stacie the Bartender.”

“I knew we weren’t exclusive,” Shay writes in My Good Side, “but it still felt like a weird in-between. It wasn’t serious, but it wasn’t nothing either.”

After the first awkward hug in 2023, Shay hoped the worst was behind her — but fate had other plans.

At the same event in 2024, she found herself face to face with Mayer again, and this time, things were no less strange.

“I didn’t even go in for the hug,” she told PEOPLE. “He went out for a handshake. I’m like, ‘Well, this is awkward, too.’”

The moment, though brief, highlights the strange dance of Hollywood exes and the long shadows cast by even the shortest of flings.

For Shay, who has since built a successful career in reality television and podcasting, the encounter was a reminder of just how surreal celebrity relationships can become once they’ve been exposed — however briefly — to the public eye. Mayer, meanwhile, has remained tight-lipped about the interaction.

A representative for the musician declined to comment on Shay’s statements, and Mayer himself has not acknowledged the story publicly.

What’s particularly telling is that Shay didn’t share these encounters to rekindle gossip, but rather to reclaim and reflect on a chapter of her life that she says was long reduced to a footnote.

Her memoir delves into more than just her time with Mayer — she also opens up about struggles with self-image, questions surrounding her sexuality, and the highs and lows of reality TV fame.

But it’s the name “John Mayer” that’s lighting up social media again — not because of scandal, but because of the sheer relatability of an awkward run-in with an ex that never quite found closure.

While their time together was brief, the fact that it continues to resurface — even in the most mundane of settings — proves just how complicated and oddly magnetic even the quietest celebrity romances can be.

In the end, Shay’s candidness in My Good Side adds another layer to a story many forgot ever happened. And as for that handshake? It may not have been warm, but it certainly left an impression.