May 2023: First Sightings
- May 25, 2023: Hailee and Josh were first spotted together in New York City. Photographs showed them leaving a black SUV, with Josh wrapping his arm around Hailee.
- This was right after rumors of Josh’s split from his longtime girlfriend, Brittany Williams, began circulating.
- The day after their first sighting, they were seen enjoying a sushi dinner with friends during Memorial Day weekend in NYC.
- An anonymous source confirmed to People that Hailee and Josh had been “hanging out for a few weeks.” The source also noted that while their relationship was new, they were “having fun.”
June 2023: Early Stages
- By June, Hailee and Josh were reportedly still in the early stages of their relationship. Sources mentioned that they were “getting to know each other” and taking things slow, especially with Josh’s training schedule.
- Us Weekly reported that despite being only a month into the relationship, things were going well. The couple was described as constantly laughing and smiling when together, with Josh being the first person Hailee had been genuinely interested in for a while.
August 2023: Going Public
- During an appearance on the Pardon My Take podcast, Josh seemed to address his relationship with Hailee. He expressed his surprise and discomfort with the attention their relationship was getting, particularly when paparazzi captured photos of them on a boat.
- He admitted to feeling insecure and frustrated by the lack of privacy, saying, “The fact that anybody cares about that still blows my mind.”
October 2023: Spending Time Together
- Hailee was spotted in East Aurora, New York, shopping with Josh’s mom at Leveled Up Buffalo. The duo picked up some Buffalo Bills merchandise, and Hailee shared a photo on Instagram with the caption, “Pinch Me,” showing her excitement about spending time with Josh’s family.
Throughout the year, Hailee and Josh have kept their relationship mostly low-key, with Hailee showing public support for Josh by attending Buffalo Bills games, often alongside Josh’s close friends like race car driver Daniel Ricciardo.
Their relationship appears to be going strong, with the pair taking things slow and enjoying their time together without rushing into anything, despite the public interest in their romance.
