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Tom Brady insists he never dated Ivanka despite Donald Trump wanting to set them up

Tom Brady has insisted he never dated Ivanka Trump despite her father's desire for them to become a power couple and eventually call the NFL star his son-in-law. 

In an awkward interview on The Howard Stern Show on Wednesday, the host asked the former New England Patriots quarterback if he had ever dated the now first daughter at Donald Trump's insistence. 

'Trump always dreamed of you marrying Ivanka, and he told me he suggested it to you — but did you ever go out with her?' Stern, 66, inquired, prompting Brady, 42, to let out an uncomfortable laugh. 

Didn't happen: Tom Brady, 42, has denied ever dating Ivanka Trump, 38, despite her father's desire to set them up in the early 2000s

Hot topic: Brady was grilled about Ivanka during his appearance on The Howard Stern Show on Wednesday. Stern noted that Donald Trump had always 'dreamed' of Brady marrying Ivanka

'That was a long time ago in my life... No, there was never that, where we ever dated or anything like that,' he said, bringing up his seven-year-old daughter, Vivian. 

'I have a daughter, so I would want my daughter to... would I ever arrange my daughter...' the incoming Tampa Buccaneers player said before Stern interjected. 

'I know it’s weird, but Trump wanted that,' the radio host said, pressing Brady further. 'He wanted Tom Brady to, let's face it, bang Ivanka and form a relationship, a power dynasty. You know that, you know I’m not making that up.' 

The six-time Super Bowl winner let out another awkward laugh before claiming Trump had never approached him about dating his daughter. 

'He never suggested that to me,' Brady said, though Stern noted that he has a tape of the now president making that very suggestion on his show. 

In 2004, Trump admitted to Stern that he had tried to set Brady up with Ivanka. 

Claim: Brady said Trump never suggested he date Ivanka despite the president publicly stating in 2004 that he wanted to set them up. Brady and Ivanka are pictured in the early 2000s

Looking back: Stern (far right) told Brady he has a tape of Trump (far left) saying he wanted him to date his daughter Ivanka 

'I think Tom’s a great guy, and I think he and Ivanka would make a great combination,' he reiterated in a 2004 interview with Playboy. 

'Look it all worked out for me anyway, I married the woman of my dreams,' Brady told Stern, referring to his model wife Gisele Bündchen. 'I think I married the most amazing woman, so I have no regrets.'

Brady and Bündchen, 39, wed in 2009, the same year Ivanka said 'I do' to her husband, fellow White House senior adviser Jared Kushner. 

He has two children with Bündchen, a son Benjamin and daughter Vivian, as well as a son Jack with his ex Bridget Moynahan.

Ivanka, 38, and Jared, 39, also have three children, a daughter Arabella and sons Jospeh and Theodore.  

While the quarterback made it clear he is happy with how things turned out, Stern couldn't resist noting that he and Ivanka would have made a good fit.  

'I could see you rather than Jared Kushner with Ivanka, honestly. I really could,' he told Brady.

Dream match: 'I think Tom’s a great guy, and I think he and Ivanka would make a great combination,' Trump said in 2004 

Old friends: Ivanka appeared on The Howard Stern Show with her father in 2006

Stern shared a similar sentiment on his show on Tuesday, saying he doesn't think Kushner is fit to be a pandemic expert or Ivanka's lover. 

'This f*****g Jared Kushner running things, it’s making me mental,' he said. '[The coronavirus pandemic] is too serious a thing to be wasting time with this kid.'

The host made it clear he doesn't have any confidence in Kushner, who is now working with the White House's coronavirus task force, and even went as far as calling him a 'sickly looking dude.'  

'How’s he f*****g Ivanka?' he asked. 'She is a primo.'

'Tom Brady looks like a guy who could handle Ivanka in bed,' he added. 'Jared Kushner, honest to God, how’s he handling that woman?' 

There has been plenty of speculation about Brady and Trump's daughter over the years, with Ivanka's mother Ivana Trump claiming in her 2017 book, 'Raising Trump,' that her ex-husband had tried to set them up. 

'At one point, Donald wanted her to date Tom Brady, the quarterback,' the book reads. 'He said, "You have to meet him!" But Ivanka wasn't into it.'

In 2017, Anthony Scaramucci was guest-hosting TMZ Live when he implied that Brady had dated Ivanka and had declined a visit to the White House at his wife's request. 

Happy: 'Look it all worked out for me anyway, I married the woman of my dreams,' Brady told Stern, referring to his model wife Gisele Bündchen

All smiles: Ivanka said 'I do' to her husband, fellow White House senior adviser Jared Kushner, in 2009, eight months after Brady married Bündchen

'There could be a little bit of jealousy there and protection and possession of Tom Brady, and she probably didn't want him to go,' the former White House communications director alleged.     

'Maybe there was a relationship between him and Ivanka at some point. Maybe it was someone else, I don't know. I just think there was a possession that caused a rub.'

Brady cited 'personal family matters' when he skipped the Patriots' White House visit in August 2017, though it may have been political. 

During his interview with Stern on Wednesday, Brady also said he had declined to speak at the 2016 Republican National Convention, explaining his 'political support is totally different from the support of a friend.'

'I didn’t want to get into all the political [arena],' he said.

The president doesn't seem to have any hard feelings, though. In fact, Brady seems to be the one who got away in his eyes. 

In 2018, the New York Times reported that Trump made several jokes that 'he could have had Tom Brady' as a son-in-law, adding: 'Instead... I got Jared Kushner.' 

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