Hailee Steinfeld and Josh Allen are prominent figures in the entertainment and sports industries, respectively. Despite their fame, this high-profile duo has maintained a level of privacy regarding their relationship. With the recent announcement of their engagement, it’s an exciting time to reflect on the romantic journey of the talented singer-actress, who is 27, and the 28-year-old quarterback for the Buffalo Bills. Let’s explore the significant milestones in their relationship thus far.

A Memorable May 2023: The Start of Something Special

On May 25, 2023, the couple was spotted together in New York City, shortly after rumors circulated about Allen’s breakup with his long-term girlfriend, Brittany Williams, whom he had been with since 2015. Photos shared by the New York Post captured Allen affectionately placing his arm around the True Grit actress, marking the first public appearance that hinted at their budding romance. This sighting followed a period of speculation regarding Allen’s relationship status, igniting interest in the new couple.

Later that same month, Hailee Steinfeld and Josh Allen shared a cozy sushi date at Sushi By Bou in Chelsea, accompanied by a few close friends. This casual outing was highlighted on social media by the restaurant’s founder, Michael Sinensky, showcasing their growing connection. The couple’s choice of dining spot added a touch of glamour to their budding romance, reinforcing their status as a fashionable duo in NYC.

Sinensky expressed his gratitude in a post, stating, “More fans of el chapo @chefsergio_nyc. Thank you, Bills’ Josh Allen, for always stopping in when in town and loving Sushi By Bou.” He further highlighted the star power of Steinfeld and her friends, calling it a special moment for the restaurant and the city, enhancing their public profile.

June 2023: Confirmation of a Romantic Relationship

As the summer approached, multiple sources began to confirm the romance between Hailee Steinfeld and Josh Allen, indicating that they had indeed started dating. This revelation generated buzz across various entertainment and sports news outlets, focusing on the couple’s chemistry and compatibility.

An insider shared with Us Weekly that Hailee and Josh had been dating for about a month, emphasizing their joyful interactions. The source described their time together as filled with laughter and happiness, illustrating a strong emotional bond. Their connection appeared to deepen as they enjoyed each other’s company, sparking excitement among fans.

Additionally, another source close to Steinfeld informed PEOPLE that the pair was still in the early stages of dating, taking the time to explore their relationship further. This gradual development suggested a thoughtful approach to their romance, a refreshing perspective for high-profile couples.

August 2023: Public Awareness and Media Attention

During a guest appearance on the Pardon My Take podcast, Josh Allen initially hesitated to discuss his relationship with Steinfeld. However, when the host brought up rumors about him “making out with his girlfriend,” he candidly remarked, “The fact that anybody cares about that still blows my mind.” His humility highlighted the challenges of navigating a public relationship amidst relentless media scrutiny.

Allen further expressed discomfort regarding photographers intruding on their private moments. He stated that such encounters left him with a “gross feeling,” underscoring the difficulties faced by celebrities in maintaining personal boundaries while in the public eye.

September 2023: Social Media Insights and Family Connections

Although neither Steinfeld nor Allen had officially confirmed their relationship at this time, Steinfeld was photographed on Instagram with Allen’s mother, Lavonne, alongside the owner of Leveled Up Buffalo, a beloved local boutique. This casual photo stirred interest and speculation among fans regarding the couple’s growing closeness with each other’s families.

October 2023: Shared Experiences and Public Appearances

On October 8, Hailee Steinfeld was seen at Allen’s game in London, capturing the attention of fans and cameras alike. Notably, Daniel Ricciardo, a well-known F1 driver, was sitting next to her, adding to the buzz of the event. This appearance showcased the couple’s willingness to support each other publicly, further solidifying their status as a couple in the limelight.

Update on this front: Danny Ric has now got his Bills gear.

*also they couldn’t get a lower third for the musician/actress to his right?!* https://t.co/VWQC3paKzV pic.twitter.com/1QM22Hh9zm

— Alaina Getzenberg (@agetzenberg) October 8, 2023

On October 13, the couple made their first official public appearance together at the Buffalo Sabres vs. New York Rangers hockey game at KeyBank Center in Buffalo, New York. Steinfeld and Allen were spotted enjoying the game from a private suite, a significant milestone that showcased their growing relationship to the public and their fans.

forget about taylor swift for a sec bc Hailee Steinfeld is at the sabres game pic.twitter.com/LRz4Iw8oX1

— Annie OD (@sweetannieod) October 13, 2023

January 2024: Playful Interactions and Family Dynamics

During the 2024 Golden Globes, a reporter cheekily asked Steinfeld how she felt about the event while holding up a No. 14 Bills jersey. Her witty response, “Real good,” perfectly captured her playful spirit, but she quickly added, “Wrong number though!” referring to the fact that the jersey belonged to Bills’ wide receiver Stefon Diggs, instead of Allen’s No. 17. This lighthearted moment emphasized her fun personality and connection to Allen’s team.

Later in January, Steinfeld was seen driving around in Laguna Niguel, California, with Josh Allen, just a week after the Bills faced a disappointing loss to the Kansas City Chiefs. This casual outing showcased their ability to enjoy normalcy amidst the pressures of their respective careers. It also demonstrated their commitment to supporting one another through both triumphs and challenges.

July 2024: Relationship Confirmation Through Social Media

After a year of dating, Josh Allen took to Instagram on July 23 to confirm his relationship with Hailee Steinfeld. His post, captioned “Onward,” included a series of photos from their summer adventures, including a romantic snapshot of the couple in Paris and a heartwarming family gathering photo. This public acknowledgment marked an important step in their relationship, solidifying their bond in the eyes of fans and followers.

The display of affection through social media not only highlighted their romantic connection but also showcased the joy they found in sharing experiences together, further endearing them to their respective fan bases.

October 2024: Community Engagement and Personal Stories

On October 12, the couple participated in the first annual Shakir Family Pet Adoption Event in Buffalo, New York. Captured in social media footage, Steinfeld shared a delightful moment of Allen holding one of the adorable dogs available for adoption, showcasing their shared love for animals and community involvement. Their attendance at this event highlighted their commitment to philanthropic efforts and public service.

On October 18, in her “Beau Society” newsletter, Steinfeld recounted a humorous story about how she and Allen narrowly avoided bad luck after they accidentally bought each other the same Christmas gift—a Miyabi Kaizen chef’s knife. This anecdote provided a glimpse into their playful and lighthearted relationship, as they navigated the quirks of gift-giving.

Steinfeld humorously noted in her newsletter, “After we exchanged our knives lol, he told me there’s an old wives’ tale that if you gift your significant other a knife you have to pay for it, otherwise it signifies the severing of a relationship.” She continued, “So we exchanged quarters so we didn’t have that bad omen,” illustrating their ability to blend tradition with humor in their relationship.

Later that month, on October 28, the couple co-hosted a lively Halloween bash for the Buffalo Bills players and their significant others. The circus-themed party was a fun affair, with both Steinfeld and Allen donning matching ringmaster costumes, showcasing their playful side and strong partnership.

November 2024: The Exciting Engagement Announcement

On November 30, 2024, the couple shared the thrilling news of their engagement through an Instagram post. The photo captured a picturesque moment of Allen on one knee, proposing amidst a romantic setting filled with candles and framed by a stunning flower-covered arch. The caption hinted that this memorable proposal took place a little over a week prior, on November 22, marked with the date “11•22•24.” This announcement not only celebrated their love but also thrilled fans who had been following their journey.