Bill Belichick’s Girlfriend Jordon Hudson Shares Glimpse Inside NYC Date Night

Jordon Hudson and Bill Belichick found love in the Big Apple.

In fact, the 24-year-old shared an intimate look into her cozy date night in New York with the former New England Patriots head coach on Instagram.

The couple, who’s 48-year age gap has recently raised a few jokes from Tom Brady and Snoop Dogg, hit all the romantic stops in their Valentine’s Day outing. In the Feb. 17 photo carousel, Jordon gushed over a red bouquet of roses Bill gave her before doing a mini tour of their hotel room, showing an overflowing bathtub and her posed in the hallway. Fittingly, the former cheerleader wore red and black for the occasion.

Jordon also shared moments from their night out, including them enjoying dinner at The River Café and picking up a few gifts at Jacob & Co.’s jewelry store.

She also hinted they stopped at Coach, as she shared a cute moment of the NFL star, 72, leading her across the street as they approached the store.

Their NYC takeover comes over a week after the duo—who began dating in 2023, shortly after Bill ended his 16-year relationship with ex-girlfriend Linda Holliday—sparked engagement rumors during the Super Bowl 2025 weekend. As the couple attended Michael Rubin’s party in New Orleans earlier this month, Jordon was seen wearing a pink-stone diamond ring.

Instagram/Jordon Hudson

While they haven’t confirmed if they’re ringing any wedding bells, that hasn’t stopped Jordon from celebrating their romance—in real life and on paper. She honored their four-year “meetiversary” in a Feb. 11 Instagram post, where she revealed they met in February 2021 after he signed her copy of Warren Goldfarb’s Deductive Logic.

Christopher Polk/Variety via Getty Images

Jordon also shared video evidence of their meet-cute and praised her boyfriend for listening to her “lengthy philosophical lectures” all these years later.

Keep reading to see other celebrity couples who aren’t phased by their major age gaps….

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Sarah Paulson & Holland Taylor

The practice of ignoring what people say about their 32-year age gap is nothing new for the actresses.

“If someone wants to spend any time thinking I’m strange for loving the most spectacular person on the planet, then that’s their problem,” Sarah told Modern Luxury in 2018 while discussing her relationship with Holland. “I’m doing just fine.”

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Heidi Klum & Tom Kaulitz

As for the former Project Runway host, she simply says auf wiedersehen to any negative comments about her 16-year age gap with the Tokio Hotel guitarist.

“My boyfriend is many years younger than me, and lots of people are questioning that and asking about it,” she shared with InStyle in 2018. “That’s really the only time when age seems to be shoved in my face and I have to give an answer for it. I don’t really think about it that much otherwise.”

And Heidi—who married Tom the following year—made it clear she’s going to continue living life on her terms.

“You have to just live a happy life without worrying too much about what people think,” the supermodel continued, “because worrying is only going to give you more wrinkles.”

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Priyanka Chopra & Nick Jonas

Meanwhile, the Quantico star has called out a double standard.

While she noted people have a lot to say about her being 10 years old than the Jonas Brother singer, she suggested this wouldn’t be the case if it were the other way around.

“People gave us a lot of s–t about that and still do,” Priyanka told InStyle. “I find it really amazing when you flip it and the guy is older, no one cares and actually people like it.”

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Sam Taylor-Johnson & Aaron Taylor-Johnson

And if you’d ask the Fifty Shades of Grey director, she’d say her 23-year age difference with the Kraven the Hunter actor just doesn’t come up in their day-to-day.

“No, it never does,” she said in a 2024 interview with The Guardian. “I mean, it’s coming up now because you’re asking. And it comes up on the outside perspective of people who don’t know us, because I guess people will always…We’re a bit of an anomaly, but it’s that thing: After 14 years you just think, surely by now it doesn’t really matter?”

Sam even pointed out her relationship with Aaron has lasted longer than her marriage to her ex-husband Jay Jopling, who is about four years older than she is.

“So, if you think of it in that way,” she continued, “then the age gap doesn’t really make any difference.”

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Michael Douglas & Catherine Zeta-Jones

Though the couple share a birthday (Sept. 25), they aren’t on the same page…of the calendar.

“My husband is 25 years older than me; that’s not a secret,” the Chicago star told WSJ. Magazine in 2021. “With any relationship, it wouldn’t be normal if there weren’t any ups and downs. The constant is love and respect.”

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Dennis Quaid & Laura Savoie

The Parent Trap alum may argue that the only ones who should be focused on his relationship with the Bonniedale Films cofounder is them. T-H-E-M, them. Get the picture?

Still, Dennis indicated he and Laura are unfazed by any attention around her being 39 years younger.

“We just don’t even notice it,” he told Today in 2021 about their age difference. “We’ve never related to someone in my life better than we do. We have such a great relationship. And love finds a way, wherever it is. And you never know, when love is coming, who that’s going to be. And you have no control over it. And we just couldn’t be happier.”

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Hilaria & Alec Baldwin

The yoga instructor has admitted she used to judge couples with big age gaps before her relationship with the actor, who is 26 years her senior.

“Alec and I are on all the lists of ‘Celebrities with the Biggest Age Differences’ and stuff like that,” she explained on her podcast Witches Anonymous in 2022. “And I would look at it and be like, ‘This older man wants some young bimbo with no opinions whatsoever. And then that younger woman is obviously a gold digger, and she obviously doesn’t even care and is just like OK, whatever, I hope you die and I’m gonna take all your money.'”

However, she’s since had a change of heart.

“Now that I’m in that relationship and people will say those things about me regularly, I’m like, ‘Oh my God, why was this trained into my head? Why was I so judgmental about other people who are literally just finding love?'” she added. “And maybe their love looks different from you, and from your love, or from what I thought love would be, but it doesn’t make it not valid.”

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Felicity Blunt & Stanley Tucci

Gird your loins because The Devil Wears Prada actor previously spoke about how he almost ended his relationship with the literary agent in the early days of their romance.

“I’m 21 years older than she is and I didn’t want to feel old for the rest of my life!” Stanley told BBC Radio 4’s Desert Island Discs in 2023. “But I knew that this was an incredibly special person.”

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Oli Green & Sienna Miller

The Alfie actress and the Lift actor know not everyone understands their relationship.

“I would imagine it would be complicated for anyone to get their head around,” Oli put it to Vogue while referencing their 15-year age gap, “but there’s been nothing but love and joy.”

And frankly, Sienna suggested nobody else needs to understand it.

“I don’t think you can legislate on matters of the heart,” she added. “I certainly have never been able to.”

Stefanie Keenan/VF24/WireImage for Vanity Fair

Jeff Goldblum & Emilie Livingston

The Jurassic Park star recalled a lighthearted moment with his Olympian wife, who is 30 years his junior.

“I said, ‘Which Beatle would I be if I was one of the Beatles?'” he remembered on The Hoda Show. “She said, ‘Rex Harrison.’ I said, ‘Wait a minute, I know we saw that My Fair Lady yesterday. I think you’re thinking of that.'”

However, Jeff noted it didn’t take Emilie long to realize she meant George Harrison.

“So there’s that kind of thing,” he noted of the couple’s age gap. But other than their differing cultural touchpoints, he continued, life together is “so far so good.”

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Rosie Huntington-Whiteley & Jason Statham

The model also doesn’t feel the need to deliver a fast and furious response to any critics of her 20-year age gap with the actor.

“His knowledge and strength are really inspiring and attractive, and that can come with a man who’s had a bit of time,” she told Glamour in 2013. “We have a connection that has nothing to do with age. Work comes and goes, but if you have someone at home who thinks you’re the greatest person in the world, that keeps you going.”

Dia Dipasupil/WireImage

David Foster & Katharine McPhee

As for how the American Idol alum feels about any judgment towards her nearly 35-year age gap with the composer? Probably so over it.

“I totally get the judgment initially, but things are never as they appear,” Katharine said on Dr. Berlin’s Informed Pregnancy Podcast in 2023. “And I’m in love with our love story, and that’s all that matters is that I’m in love with the love story.”

Instagram/Kristin Cavallari

Kristin Cavallari & Mark Estes

One thing that’s not unwritten? The way Kristin felt about her 13-year age gap with boyfriend Mark Estes.

“Me dating a 24-year-old is not something that I was searching out,” The Hills alum said on a March 2024 episode of her podcast Let’s Be Honest. “It’s not something that I ever thought would ever happen. If you guys listen to the podcast, you know I thought 30-year-olds were too young for me.”

And while Kristin said she understands how “it looks to the outside world,” she insisted Mark is “not a typical 24-year-old” and that there’s more to a person than their birth year.

“I really think age is just a number,” she continued. “It’s what you’ve been through in your life, how you were raised. There are just so many factors that go into maturity other than age.”

But months later, Kristin shared she broke up with Mark.

“I just know long-term he needs to experience life,” she said on an October episode of her podcast. “He’s young. He is. I started to feel the age a bit just with life experience. I look back when I was 24 and how much life has happened for me in between then. Those are crucial years. Those are formative years. This is when you find yourself and he needs to be able to do that.”

Still, she called their romance “the best relationship” of her life and expressed hope that Mark will realize their split was for the best.

“I know that one day he will look back and he will understand it,” she added, “and I actually think one day he will thank me.”

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Amal & George Clooney

When the Oscar winner first started crushing on the barrister, he wasn’t sure she’d feel the same way.

“I liked her, but I didn’t want to jump the shark on it,” George said on The Howard Stern Show about his early romance with Amal. “I couldn’t tell if she liked me. ‘Cause I’m 17 years older than her so she might’ve thought I was grandpa.”

However, it turns out she liked him right back and they wed in 2014.

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