SUMMARY
  • Josh Allen and Hailee Steinfeld have recently announced their engagement on Instagram.
  • Allen dated his ex-girlfriend Brittany Williams for almost a decade before calling it quits.
  • Williams found it difficult to start dating again after having been in a relationship for that long.

Wedding bells seem to be on the horizon for Josh Allen and Hailee Steinfeld as the two recently announced their engagement. The two first stirred up relationship rumors back in May 2023 and have been publicly sighted together quite a few times even though they have been quite private about their relationship.

Josh Allen
Josh Allen | Picture by All-Pro Reels, Licensed to CC BY-SA 2.0, Source: Wikimedia Commons

However, Steinfeld and Allen’s engagement looks like a whirlwind romance in comparison to the NFL quarterback’s long relationship with ex-girlfriend Brittany Williams. The former Fresno State Bulldogs cheerleader is now openly addressing how it feels to be dating again after being in a relationship for so long.

Josh Allen’s History with Ex-girlfriend Brittany Williams Dates Back to When They Were Kids

Brittany Williams
Brittany Williams | source: brittwilll on Instagram

Josh Allen and Brittany Williams first crossed paths when they were just 8 years old. Growing up in Fresno, California, they were family friends. They first met when Allen’s family invited the Williams family to his brother’s birthday, and this event was also where they had their first cute interaction.

During her appearance on Kelly Stafford’s The Morning After podcast (via New York Post), Williams said that this was the first big moment that they remembered about each other. She said that there was a baseball game going on that involved the Frasco Grizzlies and the ball ended up in the pool area which was in the outfield. She further said:

I think it was Tim Lincecum, I think he was still playing for that team, and he got the ball and it was this big ordeal, and he came and gave me the ball… And I just remember being so embarrassed like ‘oh my gosh, cooties’ … that was like our big, first moment we remember about each other.

Allen and Williams did not see each other for a long time after that. They reconnected when they were in high school and the former cheerleader asked him to be her date to her school’s Sadie Hawkins dance. However, things did not go well that night and the NFL player ended up ghosting her for a year.

Allen texted Williams after a year when they were freshmen in college. Although she was in a relationship at the time, she could not hold back once she met the footballer again. They moved in together in 2018 and dated until 2023.

Brittany Williams Found It Difficult to Get Back Into the Dating World

Hailee Steinfeld in Dickinson
Hailee Steinfeld in a still from Dickinson | Source: Apple TV+

During Brittany Williams’ recent appearance on the Martinis and Bikinis podcast, host Veronica Droulia asker her what it has been like to venture back into the dating game after being in a relationship for so long. Williams said:

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. But here I am, I am very happy now. The dating life in New York is absolutely crazy but it’s so much fun. It was so entertaining.

She stated that after a while, she had to take to step back for a bit to grow and learn about what makes her happy. The rumors about her breakup with Allen first started in April 2023 when she seemed to have completely removed every trace of their relationship from her Instagram (via New York Post).

Meanwhile, Hailee Steinfeld and Josh Allen posted a picture of their engagement on Instagram recently. The post caption mentions the date November 22, which means that they got engaged almost a week ago. The picture was taken on a grassy ridge overlooking water, with the couple surrounded by candles and framed by a large arch covered in flowers. Allen can be seen proposing to the Hawkeye actress on one knee.

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