Weird Things About Hailee Steinfeld And Josh Allen's Romance

Hailee Steinfeld and Josh Allen have quickly become one of the most talked-about couples both in the entertainment scene and the sports world. After what seemed to be just a fun, casual fling, the actor and Buffalo Bills quarterback surprised everyone and their mother by announcing their engagement on Instagram in November 2024. After all, it was quite the shocker: the two had been dating for just over a year after initially being spotted together on a date in May 2023. At the time, Allen had just broken up with his longtime girlfriend, Pilates instructor and influencer Brittany Williams, following a nearly 10-year relationship. Hmm... Sound familiar?

Aside from their fast-moving romance, there are other somewhat strange things about Steinfeld and Allen that we can't help but notice, such as their unlikely coupling (how exactly did this pair happen?) and reluctance to publicly discuss their relationship. During an interview with E! News at the 2024 Golden Globes, Steinfeld appeared to shut down a question about her NFL-star boyfriend after host Keltie Knight asked, "What is it about a sporty man?"  Steinfeld responded, looking visibly uncomfortable despite her smile, "Listen, what isn't it about? Come on now." (No further comments? Nada?)

Then there are those rumors that Allen may have cheated on his ex-girlfriend with the Oscar nominee, given the suspicious timeline of their relationship. Between this and the unanswered questions about their unexpected pairing, there's no shortage of weird details surrounding Steinfeld and Allen's romance.

Josh Allen's rumored romance with Hailee Steinfeld came hot on the heels of his breakup with Brittany Williams sometime in May or April 2023. Although the former couple never officially confirmed their split, hawk-eyed fans began to suspect trouble after noticing that Williams had unfollowed Allen on her social media that April. Weeks later, he was photographed with Steinfeld while out in New York City, igniting speculation about them being a new item. A source told Us Weekly in July that the pair had indeed been seeing each other for weeks, and things were looking very promising. "It's going really great," they said. 

Considering the timing of their romance, some couldn't help but wonder whether Allen had cheated on his ex-girlfriend to be with Steinfeld. On Reddit, one user tried to connect the dots and speculated about a possible overlap between the two relationships. "I did some Googling and it looks like he was with [Brittany] for 8 years and they broke up in April 2023, then in May 2023 he and Hailee 'started' dating," the user remarked. But regardless of whether cheating was involved or not, things still happened so fast that fans couldn't help but feel bad for Allen's ex. "At minimum, I think he met Hailee and became very motivated to become single asap," one Redditor also opined. "He dropped his ex like a bad habit and never looked back."

Josh Allen and his ex-girlfriend, Brittany Williams, have known each other since they were kids — literally. In a candid episode of Kelly Stafford's "The Morning After" podcast in 2022, Williams recalled first meeting Allen at a birthday party for his brother when they were just about eight years old. They reconnected in high school before officially getting together during their freshman year of college at Fresno State University. Throughout his career, Williams was incredibly supportive of Allen and was a constant presence at his games, and the two even lived together for several years. Just about everyone thought their relationship would lead to something more serious, so it came as a shock when they split, and Allen quickly moved on with Hailee Steinfeld.

Appearing on the "Martinis and Bikinis" podcast in February 2024, Williams opened up regarding her shady split from Allen and how she's coping post-breakup. "I was with my ex boyfriend for 10 years. I would say that coming into the dating world was very, very, very difficult for me at first, because I'm just like, I never thought I would be here again." She also admitted, "It is crazy out here on these streets, I'll just say that. But it's beautiful, because it makes you realize everything you want and makes you not settle for anything more than that." Ten years with Williams didn't get the Buffalo Bills QB to put a ring on it, but only a year with Steinfeld, and he's ready to fully commit? What gives?

Since they started dating, Hailee Steinfeld and Josh Allen have mostly avoided the spotlight and have purposely kept their relationship private (perhaps too private). However, in an interview on the "Pardon My Take" podcast, Allen finally addressed his rumored romance with Steinfeld and how he feels about the constant attention surrounding their relationship. "The fact that anybody cares [who I'm dating] blows my mind," he expressed. He also reacted to snaps of them taken during their Mexican getaway in July 2023, saying he felt a "gross feeling [and] insecurity" seeing those photos. "I was like, 'What is wrong with people?'"

Whereas Steinfeld had gotten used to the paparazzi hounding her, a source told Life & Style in August 2023 that Allen wasn't prepared for this kind of public attention. "It really upsets Josh," they claimed. "Anytime people recognize them and want to take pictures, he gets tense and it spoils the mood." They added that Steinfeld is worried this would eventually become a problem in their relationship. "She really likes him, but if he can't get used to the attention, it's not going to last."

Notably, the pair only confirmed their relationship status about a year after rumors of their romance first surfaced in 2023. Allen shared on Instagram a photo of himself and Steinfeld with their heads turned toward the Eiffel Tower in Paris. He also included snaps of Steinfeld with his family and during their European summer vacation in the photo carousel, which he captioned "Onward," alongside a "rock on" emoji. 

Much like Taylor Swift and Travis Kelce, Hailee Steinfeld and Josh Allen come from two vastly different and seemingly incompatible worlds. Steinfeld grew up in the Hollywood spotlight as a former child actor who shot to stardom for the Oscar-nominated film "True Grit" in 2010. Meanwhile, Allen rose to prominence as a star quarterback for the Buffalo Bills after being drafted into the NFL in 2018. Following reports that the two were dating, many expressed their surprise at this strange and unexpected coupling, with one Reddit user pointing out, "They sort of look mismatched as a couple. I don't know if that makes sense?" Another chimed in, saying, "This was not on my 2023 bingo card. I dunno how I feel about this."

Regardless of their obvious differences, a source close to the pair revealed that Steinfeld and Allen have bonded over their shared family values and strong work ethic. They were also said to be on the same page when it comes to handling their relationship, according to the insider who spoke to People: "They want to protect their relationship and keep it private." Before Allen, Steinfeld's dating history includes PR executive-slash-influencer Cameron Smoller and former One Direction member Niall Horan, whom she quietly dated for less than a year. In the wake of the dating rumors, an insider told Us Weekly in 2023 that "Josh is the first guy in a while [Hailee's] been really interested in."

Hailee Steinfeld and Josh Allen got engaged on November 22, 2024, after dating for just less than two years. The "Pitch Perfect 2" star and Buffalo Bills player shared the news through a joint Instagram post that included a glimpse of Allen's stunning and elaborate proposal. However, their excitement was quickly overshadowed when Allen's ex-girlfriend made a cryptic post in response to their viral announcement. After one user asked if she had found "the next pro athlete yet," Allen's ex, Brittany Williams, replied rather sourly, "Luckily my boyfriend owns a team and doesn't play for one. Don't have to be with another brain-dead CTE athlete," according to The New York Post.

Williams later retracted her statement by claiming that she had been hacked on Instagram repeatedly. "Trying to get it resolved," she wrote on her Instagram Story, per People. "If anyone has any tips please Imk." However, fans didn't buy her excuse and dragged Williams for secretly being a hater. "Couldn't hide her jealousy a little better?" one X user responded, while another took a swipe at Williams by comparing her to Travis Kelce's ex, Kalya Nicole: "She should hang out with Kelce's ex and they can reminisce about being relevant."

As for Steinfeld and Allen, the happy couple doesn't appear to be at all bothered by the drama as they discussed their engagement on Steinfeld's Beau Society newsletter. Both expressed their excitement as they recalled the events leading up to Allen's proposal, which Steinfeld described as "the most magical day of [my] life," according to Sports Illustrated. Meanwhile, Allen said about being engaged to Steinfeld, "It feels unbelievable to be engaged to someone who is so special and loving and caring and gorgeous and fun and happy."