Buffalo Bills quarterback Josh Allen had an unexpected moment of levity during his first press conference following the announcement of his massive new contract extension. While the focus was primarily on his six-year, $330 million deal, one reporter caught Allen off guard with a surprising—and personal—question: Would the payday lead to an upgrade on fiancée Hailee Steinfeld’s engagement ring?

Earlier this week, Allen signed a record-setting extension that includes an astounding $250 million in guaranteed money, securing his future with the Bills and making him one of the highest-paid players in NFL history. The deal is expected to keep Allen in Buffalo for the remainder of his career, something the veteran quarterback has openly hoped for.

Though Allen now ranks among the NFL’s elite earners, he showed a grounded perspective when asked about the contract’s staggering numbers.

“It’s strange to say, but what’s an extra $5 million going to do for me that I can’t already do?” Allen said. “It didn’t seem like a huge deal to me. I just wanted to make sure it wouldn’t negatively affect the team’s salary cap.”

While the financials made headlines, it was the unexpected ring question that brought some lightheartedness to the press conference.

“A bigger ring, you said?” Allen responded, laughing. “No, I think she’s happy with the one she has.”

Allen and actress Hailee Steinfeld got engaged in November along the scenic California coastline. The two were first linked in the spring of 2023 and have kept their relationship largely private. However, Steinfeld recently joined Allen for a rare public appearance at the NFL Honors, where the couple walked the red carpet together.

Reflecting on this exciting chapter in his personal life, Allen spoke with heartfelt appreciation.

“I feel incredibly blessed with everything happening in my life, especially finding the person I want to spend it with,” he said. “Once you have that part of your life figured out, it feels like everything else just falls into place.”

Allen’s off-field joy complements what has been a career-defining year on the field. The Bills’ franchise QB earned the 2024–2025 NFL MVP award following a standout season. He recorded 41 total touchdowns—one of which came as a receiver—and threw just six interceptions, the lowest mark of his career.

Buffalo finished the regular season with 13 wins and another playoff berth, though they ultimately fell short of a Super Bowl appearance. Still, Allen’s leadership and performance reaffirmed his status as one of the NFL’s premier quarterbacks—and now, one of its most committed.

With his future secured in Buffalo and his relationship with Steinfeld stronger than ever, Allen’s life appears to be firing on all cylinders.