The Hailee Steinfeld Josh Allen Timeline: What Really Happened

Honestly, it feels like forever ago when those first blurry paparazzi shots of Hailee Steinfeld and Josh Allen in NYC hit the internet. It was May 2023. At the time, nobody really knew if it was a "thing" or just a random dinner between two people who happen to be very famous. Fast forward to now, and they aren't just a thing—they’re one of the most stable power couples in the spotlight, having navigated a whirlwind three years that transformed a rumored fling into a marriage and a growing family.

Most people get the timeline wrong because these two are notoriously private. They didn't do the whole "red carpet debut" two weeks in. Instead, they spent months dodging cameras and dropping tiny hints in newsletters. If you've been trying to keep track of how the Buffalo Bills quarterback and the Hawkeye star went from sushi dates to "I do," here is the actual breakdown of the Hailee Steinfeld Josh Allen timeline.

The Summer of "Are They or Aren't They?" (2023)

It started on May 25, 2023. They were spotted in New York City, looking casual but definitely together. Two days later? Spotted again. Then came the infamous dinner at Sushi By Bou in Chelsea. The restaurant owner actually posted a photo of them on Facebook, and fans noticed Josh’s arm was around Hailee.

The internet went into a bit of a tailspin. Josh had recently split from his long-term girlfriend, Brittany Williams, and people were quick to judge the "rebound" speed. But insiders told People magazine pretty early on—specifically May 29—that they had already been "hanging out for a few weeks." It wasn't a one-night thing.

By the Fourth of July, the "rumor" part of the relationship was basically over. Photos surfaced of them on a boat in Los Cabos, Mexico. It was peak PDA. We’re talking kissing in the water, Hailee in a bucket hat—the works. When Josh later appeared on the Pardon My Take podcast in August, he didn't confirm her name, but he did admit that the paparazzi following them felt "gross." He didn't deny she was his girlfriend, though. That was the first real sign this was serious.

Football Season and Family Ties

Things moved fast behind the scenes. In September 2023, Hailee was spotted shopping in Buffalo with Josh’s mom, Lavonne. That’s a huge milestone. You don't go merch-shopping with the mom if you're just "hanging out."

Key Moments Late 2023

• October 12, 2023: Their first "official" public date at a Buffalo Sabres game. They sat in a suite, looked cozy, and finally stopped hiding from the Jumbotron.
• The Knife Incident: In her Beau Society newsletter, Hailee later shared a weirdly cute story. For Christmas 2023, they accidentally bought each other the exact same gift: a Miyabi Kaizen chef’s knife. Apparently, there’s an old superstition that gifting a knife severs a relationship, so they exchanged quarters to "buy" the knives from each other and break the curse. Kinda superstitious, kinda adorable.

The Year of the "Hard Launch" (2024)

2024 was when the floodgates opened. During the off-season, they traveled to Paris. This is where the famous "split pants" story happened. Josh posted on X (formerly Twitter) about ripping his pants during a romantic dinner and having to rush into a hotel while Hailee stayed behind to talk to fans.

On July 23, 2024, Josh finally made it Instagram official. He posted a carousel of photos, including one of them looking at the Eiffel Tower. He captioned it "Onward." That was the moment the world stopped asking "if" and started asking "when."

Then came the engagement. On November 22, 2024, Josh proposed in Malibu. It was a whole production—candles, a massive floral arch, and the Pacific Ocean in the background. They didn't announce it immediately, waiting until Thanksgiving weekend to share the news on Instagram with the caption “11•22•24.” Hailee later told Who What Wear that she was completely blindsided by the proposal, even though she had jokingly asked him earlier that day when they were getting married.

MVP Wins and Wedding Bells (2025)

The start of 2025 was a heater for the couple. In February, Josh won the NFL MVP award. They made their red carpet debut at the NFL Honors in New Orleans, and in his acceptance speech, he called Hailee his "rock."

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They didn't wait long to tie the knot. On May 31, 2025, Hailee and Josh got married at San Ysidro Ranch in Montecito, California. It was an intimate, private ceremony. Hailee described it in her newsletter as a day where "love was running through the veins of every tree."

The Latest Chapter: 2026 and Beyond

By the end of 2025, the couple shared their biggest news yet. On December 12, Hailee announced via her Substack that she was pregnant. She later showed off her baby bump at the 2026 Golden Globes, looking incredible in a custom gown.

As of early 2026, they are preparing for the arrival of their first child while Josh continues his run with the Bills. It’s been a remarkably fast transition—from a random NYC sighting to a married couple expecting a baby in less than three years—but they’ve managed to keep a level of normalcy that most Hollywood-NFL pairings struggle with.

Insights for Fans and Followers

If you're following the Hailee Steinfeld Josh Allen timeline, there are a few things to keep in mind regarding how they handle their public life:

• Newsletter First: If you want the real tea, Hailee’s Beau Society newsletter is where she actually shares the personal details, not her main Instagram grid.
• Privacy is Priority: Despite being high-profile, they rarely do joint interviews. They prefer to support each other from the sidelines—literally.
• Buffalo is Home: Don't expect them to be LA fixtures. They spend a significant amount of time in Western New York, and Hailee has fully embraced the "Bills Mafia" lifestyle, often seen in vintage team gear.

Keep an eye on the Beau Society updates throughout 2026 for the first photos of the "Baby Bill" once he or she arrives.