Actress and singer Hailee Steinfeld is making the most of her NFL star fiancé Josh Allen’s free time following the rigorous Super Bowl season.
On the evening of February 25, 2025, the newly engaged lovebirds were spotted stepping out for an intimate dinner date in Milan, Italy, after attending the Haute Couture 2025 Milan Fashion Week.
The Pitch Perfect star looked chic in a black leather jacket featuring a hood and a unique leather scarf design stitched into the collar. She paired it with black pants, a matching small leather handbag, and chunky gold hoop earrings.
The Buffalo Bills quarterback perfectly coordinated his outfit with his fiancée’s, opting for an all-black ensemble that included relaxed-fit joggers, a plain round-neck T-shirt, and a Prada windbreaker. He added a pop of color to his dark look with white sneakers.
In paparazzi-captured images, the couple was seen stepping out of their hotel, heading toward their parked getaway car. Hailee led the way, with Josh closely following behind.
Before getting into their car, the Love Myself singer warmly waved to the assembled fans and paparazzi, flashing a bright, toothy smile.
Hailee Steinfeld & Josh Allen headed to dinner in Milan tonight 🤍
— Chicks in the Office (@ChicksInTheOff) February 26, 2025
(📸 BACKGRID) pic.twitter.com/qoOPcj3cGo
Hailee Steinfeld And Josh Allen Make Red Carpet Debut After Engagement
Just a few weeks before their Italian vacation, Hailee and Josh made their stunning red carpet debut as an engaged couple on the night of February 6, 2025.
They attended the NFL Honors in New Orleans in support of Allen’s nomination for the NFL’s 2025 Most Valuable Player Award—the league’s top honor—which he also won that night.
During his acceptance speech, the NFL star poured his heart out, expressing deep gratitude for Steinfeld’s unwavering support throughout his career. Acknowledging her significant role in his success, Allen turned to her with a loving gaze and said,
“Last but not least, my fiancée Hailee—you’ve been my rock, you’re my best friend. I would not be standing on the stage if it weren’t for you”.
MVP MVP MVP 👏@BuffaloBills' Josh Allen wins the AP Most Valuable Player Award 🏆 pic.twitter.com/EC5Ocf3uE6
— FOX Sports: NFL (@NFLonFOX) February 7, 2025
Josh Allen and Hailee Steinfeld first started dating in May 2023 after a chance encounter. After a year of keeping their romance private, they made their relationship Instagram official in July 2024.
In November of that same year, the lovebirds got engaged and have been thriving in their relationship ever since.
From red carpets to romantic getaways, Hailee Steinfeld and Josh Allen are proving that their love story is just getting started.
With wedding bells on the horizon, this power couple is making every moment count—whether on the field or in fashion capitals of the world!