Josh Allen is living the dream. Over the past 100 days, the Buffalo Bills quarterback has reached incredible milestones—both in his personal and professional life. From getting engaged to Hollywood star Hailee Steinfeld to winning the NFL MVP award and signing a record-breaking contract, Allen has cemented his place as one of the most successful athletes of his generation.

As the dust settles on this whirlwind period, the focus now shifts to what comes next. With a massive extension securing his future and a wedding on the horizon, Allen’s next chapter is shaping up to be just as exciting. Let’s take a deep dive into his remarkable journey.

A Love Story Fit for Hollywood: Allen and Steinfeld’s Engagement

Josh Allen and Hailee Steinfeld’s relationship first made headlines in mid-2023 when the couple was spotted together in New York. Steinfeld, an award-winning actress and singer known for roles in True Grit, Pitch Perfect 2, and Hawkeye, had previously kept her love life private. However, her chemistry with Allen quickly became a hot topic among fans and media alike.

After dating for over a year, Allen proposed on November 29, 2024, in a private and romantic setting. While details of the proposal remain scarce, sources close to the couple describe it as intimate and heartfelt—exactly what Steinfeld had wanted.

The engagement was met with enthusiasm from both the NFL and Hollywood communities. Bills fans welcomed Steinfeld as part of the team’s extended family, and celebrities congratulated the couple on social media. Their upcoming wedding, set for May 31, 2025, is expected to be one of the most talked-about celebrity events of the year.

Allen’s MVP Season: A Performance for the Ages

While planning a wedding is no easy feat, Allen’s focus on the football field never wavered. The 2024 NFL season was arguably the best of his career, and his dominant performances week after week solidified his place as one of the league’s premier quarterbacks.

Regular Season Dominance

Allen finished the 2024 season with:

• 4,731 passing yards
• 39 passing touchdowns
• 9 interceptions
• 672 rushing yards
• 14 rushing touchdowns

His ability to thrive as both a passer and a rusher made him a nightmare for opposing defenses. The Bills, powered by Allen’s heroics, ended the season with a 13-4 record, securing the AFC’s No. 2 seed in the playoffs.

Playoff Brilliance

Buffalo’s postseason journey was another showcase of Allen’s talent. In the divisional round, he led a fourth-quarter comeback against the Kansas City Chiefs, throwing for three touchdowns in the final 10 minutes to secure a 34-31 victory. Though the Bills ultimately fell short in the AFC Championship against the Baltimore Ravens, Allen’s efforts did not go unnoticed.

On February 6, 2025, Allen was named NFL MVP, beating out Lamar Jackson and Patrick Mahomes for the award. It marked a crowning achievement for the quarterback, proving that he had ascended to the very top of the league.

The Contract That Changed Everything

Success in the NFL often translates into financial rewards, and Allen’s MVP season set him up for an unprecedented payday. On March 9, 2025, the Buffalo Bills signed their franchise quarterback to a six-year, $330 million contract extension, including $250 million in guaranteed money—the highest guarantee ever given to an NFL player.

Breaking Down the Historic Deal

Allen’s contract shattered multiple records:

• Highest total contract value for a quarterback ($330 million over six years)
• Most guaranteed money in NFL history ($250 million)
• Largest signing bonus ever given to a player ($95 million)

ESPN’s Adam Schefter reported that the deal was structured to give Buffalo flexibility in free agency while ensuring Allen remained one of the highest-paid players in the league.

What It Means for the Bills

By locking up Allen for the long term, the Bills have secured their Super Bowl window for years to come. With the salary cap expected to rise, Buffalo’s front office is now in a prime position to build around Allen, bringing in elite weapons and bolstering the offensive line.

Head coach Sean McDermott emphasized Allen’s leadership in the team’s official statement:
“Josh is the heart and soul of this team. His work ethic, passion, and competitive drive set the tone for everyone in this building.”

Allen’s Next 100 Days: Wedding Bells and the 2025 Season

While the past few months have been filled with professional accolades and contract negotiations, Allen’s next focus is on his upcoming wedding to Hailee Steinfeld. Bills offensive lineman Dion Dawkins recently revealed on Good Morning Football that the couple will tie the knot on May 31, 2025.

With the financial security of his new contract, Allen certainly has a comfortable budget for wedding planning. Insiders suggest the couple is considering a destination wedding, possibly in Italy or the Caribbean, but no official details have been confirmed.

Offseason Training and Preparation

Even with wedding plans in motion, Allen remains dedicated to his craft. His offseason regimen includes:

• Private QB workouts with Jordan Palmer
• Strength and conditioning training in California
• Throwing sessions with Stefon Diggs and Dalton Kincaid

Buffalo’s 2025 season kicks off in September, and expectations have never been higher. The Bills are considered Super Bowl favorites, with Allen leading a high-powered offense that now includes newly acquired free agent wide receiver Tee Higgins.

The Legacy Allen is Building

At just 28 years old, Allen is already crafting a Hall of Fame-worthy career. Since entering the NFL in 2018, he has rewritten Buffalo’s record books, becoming the franchise leader in passing touchdowns, total yards, and playoff wins.

His combination of elite arm strength, mobility, and leadership has drawn comparisons to some of the all-time greats. With his new contract ensuring he remains a Bill for life, Allen now has one goal left—bringing a Super Bowl to Buffalo.

Where Does Allen Rank Among Active Quarterbacks?

While Allen’s MVP award and contract solidify his elite status, the ongoing debate remains—where does he rank among today’s quarterbacks?

• Patrick Mahomes (Chiefs): 3x Super Bowl Champion, the league’s gold standard
• Josh Allen (Bills): MVP, elite dual-threat QB, still searching for first ring
• Joe Burrow (Bengals): Cool under pressure, but injury concerns remain
• Lamar Jackson (Ravens): Two-time MVP, but postseason struggles persist
• Jalen Hurts (Eagles): Dual-threat ability, but needs more consistency

If Allen can add a Super Bowl ring to his resume, he will officially enter Mahomes’ territory as one of the greatest QBs of his generation.

Final Thoughts: The Best is Yet to Come

Josh Allen’s last 100 days have been nothing short of extraordinary. He has reached personal milestones with his engagement to Hailee Steinfeld, achieved professional success by winning NFL MVP, and secured his future with a historic contract extension.

Yet, for all that he has accomplished, Allen remains as hungry as ever. With his wedding just around the corner and the 2025 NFL season approaching, the next chapter of his career—and life—is shaping up to be just as thrilling.

Buffalo fans have long dreamed of a Super Bowl parade down Main Street. If Allen continues on his current trajectory, that dream may become a reality sooner rather than later.