Married with trivia: This Jeopardy! couple hopes to make game show history

Jason Singer and Susan McMillan aren’t just a married couple — they’re trivia soulmates with a shared dream. As Jason steps onto the Jeopardy! stage on July 1, he’s not only chasing personal glory but hoping to help the pair become the first-ever husband and wife duo to both win the beloved game show after marriage. With history — and a bit of healthy competition — on the line, this couple’s journey is a testament to love, smarts, and relentless preparation.

A shared dream, a personal milestone

For Jason Singer, his Jeopardy! debut on July 1 is more than just a trivia showdown — it’s the culmination of years of study, shared ambitions, and deep admiration for a very special competitor: his wife.

Singer, a former journalist turned real estate agent, first discovered his love for trivia in childhood, memorizing state capitals and arithmetic tables for fun. But it was during his relationship with Susan McMillan, also a former reporter, that this passion found a true partner. The couple bonded over their mutual love of Jeopardy!, even joking that they’d only apply when they hit their “peak level of intelligence.”

“Since we started dating, we’d always said, ‘When we’re smart enough, we’ll do this,’” Singer shared. “It became part of the rhythm of our relationship.”That long-standing pact will finally be put to the test as Singer competes on the July 1 episode, years after McMillan already proved her trivia prowess by winning $35,600 during her 2021 appearance. Now, Jason is hoping to follow in her footsteps — and create a unique mark in Jeopardy! history.

Making trivia history — together

The couple’s shared goal isn’t just to win individually. They’re aiming for something unprecedented: becoming the first married couple to have both been Jeopardy! champions after getting married.

“We’re hoping to become the first-ever couple to have been married first and then gone on to both be Jeopardy! champions,” Singer said. “So some fun history is at stake.” It’s a title that would reflect not just their individual knowledge, but the years of teamwork that have gone into preparing for this moment. The duo even developed their own online database to track trivia topics, and used flashcards to drill themselves on everything from Shakespearean characters to U.S. vice presidents.

And while Singer approaches the show with excitement, he also injects a sense of humor into the pressure: “Tune in, root me on, and laugh at some of my almost-certain-to-occur dumb answers,” he joked, noting that no contestant is immune to mental blanks when the cameras roll.

Behind every great trivia champ…

According to Singer, part of his confidence heading into the game comes from a unique advantage: daily scrimmages with what he calls the “Michael Jordan of trivia.” “I’ve gotten to practice against the Michael Jordan of trivia every day of my life for the last 15 years,” he said of McMillan. “And that is an advantage nobody else in the world has — because I’m the only person lucky enough to be married to Susan.”

McMillan, for her part, agrees. But she also sees how her win in 2021 pushed her husband to double down on preparation. “The experience I had made him want to prepare even harder, to have no gaps in his game,” she said.

Their study sessions aren’t just about winning — they’re an extension of their connection. The trivia flashcards, the debates over obscure presidents, and the celebration of random facts have become a language of love for the couple, enriching their relationship as much as their knowledge base.

A race against time — and trivia fate

The couple’s dream of competing on Jeopardy! was long-held, but it gained urgency after host Alex Trebek’s cancer diagnosis was announced in 2019. Suddenly, a goal that had once seemed distant felt pressing.

“We weren’t sure if he would survive, if the show would continue,” Singer explained. “And even if the show did go on, we didn’t know what form that would take.” When McMillan finally got her shot at the game, Trebek had passed, and COVID-19 restrictions meant Singer couldn’t attend in person. Watching her win remotely, though, fueled his determination to make his own mark — and perhaps, to honor the timeline they’d once envisioned sharing together.

That sense of shared purpose continues to power his mindset going into the game. While both McMillan and Singer pursued their Jeopardy! dreams individually, they’ve always seen them as chapters in the same story — one that blends intellect, timing, and love.

More than just a game

As he prepares to make his mark on one of America’s most iconic quiz shows, Singer is already thinking beyond buzzers and daily doubles. Yes, he wants to win — but more than that, he wants to add something meaningful to a legacy he and his wife have been quietly building for years.

“This has been a multi-year dream in the making,” Singer said. “I’d like to be invited back one day, so please tune in — and let’s set some viewership records.” Win or lose, his appearance is already a win for the trivia-loving couple who turned a shared passion into something bigger. Whether they ultimately claim the title of Jeopardy!’s first post-marriage champion couple or not, they’ve already proven one thing: in the game of love and knowledge, they’re playing on the same team.