Hailee Steinfeld and Fiancé Josh Allen’s Rare Date Night in Italy Will Leave You Starving for More

Hailee Steinfeld and Josh Allen didn’t fumble their latest date night. 

The “Starving” singer and Buffalo Bills quarterback stepped out for dinner while on vacation in Italy during Milan Fashion Week 2025, and the couple certainly arrived dressed to impress for the haute couture occasion. 

During their Feb. 25 outing, Hailee wore a leather jacket with a matching leather scarf and black pants as she and Josh headed out to the restaurant. To top off her ensemble, the 28-year-old rocked chunky gold earrings and wore her hair in a sleek, low bun. 

As for Josh—who announced his engagement to Hailee in November following over a year of dating—the NFL star coordinated his outfit with the Pitch Perfect alum, opting for an all-black ensemble that included joggers, a plain shirt and a Prada windbreaker. 

But dinner wasn’t the only adventure the pair went on together since touching down in Europe.