Josh Allen & Hailee Steinfeld's Relationship Timeline From Lowkey Couple To Romantic Engagement

Hailee Steinfeld and Josh Allen are spending their holiday season this year as an adorable, newly engaged power couple, and their heartfelt relationship has been the stuff of storybook romances. The Oscar-nominated actress and the NFL pro announced their engagement in a swoon-worthy Instagram post on November 29, which showed Allen popping the question with a gorgeous proposal overlooking the beach while surrounded by candles and a stunning pink flower archway. The caption simply revealed that the special moment had gone down on November 22.

The news was met with messages of celebration and congratulations from the couple's famous friends and supportive fans. The engagement came as a surprise to some, as Steinfeld and Allen have managed to keep their relationship largely out of the public's prying eye. While Steinfeld is an avid social media user, she has made sure to keep her private life out of the spotlight. However, looking back at the low-key start to their courtship and their whirlwind romance, it's clear just how deeply in love Allen and Steinfeld truly are.

Rumors began to circulate that Hailee Steinfeld had a new man in her life back on May 25, 2023, when she was spotted out and about in New York City with Buffalo Bills quarterback Josh Allen. The casual date night came shortly after reports that Allen and his longtime girlfriend, Brittany Williams, had called it quits. Meanwhile, Steinfeld had, to this point, largely kept her dating life out of the headlines, apart from a brief relationship with singer Niall Horan, which only lasted for a few months during the summer of 2018.

Just two days later, Steinfeld and Allen were photographed once again, this time rocking color-matching all-black ensembles as they enjoyed yet another romantic evening in the Big Apple. An eyewitness told Entertainment Tonight at the time that the pair "arrived together at around 9:30 p.m. and enjoyed cocktails and omakase." During their dinner date, Allen was seen getting behind the bar and serving Steinfeld, and the couple "looked sweet together, and it seemed like they had a great time."

Hailee Steinfeld and Josh Allen hadn't officially confirmed that they were dating by July 2023, but their joint trip to Los Cabos for the 4th of July weekend did the talking for them. They were photographed packing on some PDA while enjoying their time at the idyllic vacation spot. Steinfeld and Allen were spotted by paparazzi making out in the pool at the hotel, essentially erasing any doubt about their relationship status.

Several months later, Steinfeld and Allen were photographed in the stands at an NHL game, enjoying a date night while watching the Buffalo Sabres take on the New York Rangers. The actor was spotted by fans cheering and getting deeply involved in the match, and photos of the "Hawkeye" star began to make the rounds on social media. "Forget about Taylor Swift for a sec bc Hailee Steinfeld is at the Sabres game!" one user wrote on X, formerly Twitter, as others in the comments weighed in on her romance with Allen, comparing their low-key relationship to Taylor Swift and Travis Kelce's spotlight-stealing courtship.

Just over a year after Josh Allen and Hailee Steinfeld were first romantically linked, the duo finally confirmed their relationship with an Instagram post that Allen shared on July 23, 2024. The NFL pro shared a carousel of photos that began with a sweet snap showing himself and Steinfeld looking away from the camera toward the horizon with the Eiffel Tower taking center stage between them. It also included a photo of himself and Steinfeld at an unspecified family event alongside other beaming friends. Allen captioned the post simply, "Onward."

While Steinfeld didn't take this opportunity to confirm their romance on her own account, she did confirm that it was, in fact, her in the photo taken on the Paris rooftop (since her face wasn't visible in Allen's first post). Steinfeld shared a trio of photos of herself on the same rooftop in the same outfit to Instagram in April, cryptically captioning the post with the iconic "Casablanca" quote, "We'll always have Paris."

Three months after Josh Allen officially confirmed his romance with Hailee Steinfeld on Instagram, the actress returned the favor, posting cute pics from their circus-themed Halloween bash to her own Instagram. Steinfeld and Allen hosted a lavish celebration while decked out in bright red big top ringleader outfits, surrounded by balloons, vintage circus clown backdrops, and a slew of bespoke custom decorations emblazoned with their names. The event, which was held in Orchard Park, New York, was attended by many of Steinfeld's famous friends, as well as Allen's Buffalo Bills teammates,

Steinfeld's post included photos of the party and its elaborate layout, as well as snapshots of herself and Allen posing in their picture-perfect costumes. The final shot shows the two lovebirds sharing a sweet kiss — although Allen is blocking their faces with his black top hat. It was a sweet way to formally introduce their relationship to the world, and it came just over a month before they took the next big step in their romance.

After dating for a year and a half, Josh Allen surprised his lady love with a stunning beachside proposal. Dropping down on one knee in front of a gorgeous pink floral arch with the gentle ocean waves cresting in the soft afternoon light, Allen asked Hailee Steinfeld to marry him — and she said yes. Allen and Steinfeld shared a photo of the dream moment in a joint post to Instagram, which they simply captioned "11•22•24" flanked on either side by two blue infinity emojis. It was a simple, understated announcement befitting their lowkey and largely private romance.

The response from their friends and family was overwhelmingly supportive and excited. Fellow NFL star Travis Kelce (whose relationship with Taylor Swift proves he knows a thing or two about high-profile romances with famous entertainers) commented, "Congratulations!!!" Meanwhile, actress Bailee Madison wrote, "Forever!!!!!... so happy for you both and can't wait to see the magic and love you fill your life together with!" Steinfeld's "Pitch Perfect 2" co-star Rebel Wilson also chimed in, sharing the "biggest congratulations."

Now, only time will tell just how star-studded Steinfeld and Allen's eventual wedding will be or if they'll keep their nuptials as understated as the rest of their romance.