Tom Brady leaning on Leonardo DiCaprio to 'have fun' post divorce with Gisele Bundchen - "They really clicked"

Former NFL quarterback Tom Brady and Academy Award-winning actor Leonardo DiCaprio are starting to become good friends.

An insider explained to OK! Magazine’s Molly Claire Goddard:

"It was a little awkward at first, but once they got past the whole Gisele thing, they really clicked. And the fact is, there’s an opening in Leo’s circle! Tom wants to get out and have fun, and Leo’s more than happy to play the pied piper."

It’s a weird connection because DiCaprio dated Gisele Bundchen from 1999 to 2005. The Brazilian supermodel started dating Tom Brady in December 2006. Three years later, the power couple married in Santa Monica, California.

Brady and Bundchen announced their divorce in October 2022. They have two children: 13-year-old Benjamin Rein and ten-year-old Vivian Lake.

With Brady being a bachelor again, he is building a link with one of his ex-wife’s previous flames.

The insider added:

"Now that Tom is single and out on the social circuit in Miami, he’s been getting close with a lot of people Leo knows. That’s how they got connected."

Last month, DiCaprio and Brady were on the same yacht in Sardinia, Italy, as guests on entrepreneur Bert Hedaya’s birthday. Restaurant mogul David Grutman posted a photo on Instagram.

Brady, DiCaprio, and Grutman also attended Joe Nahmad and Madison Headrick’s wedding, reportedly worth $12.9 million.

Meanwhile, Leonardo DiCaprio dated Israeli model Bar Refaeli after Bundchen. Their relationship lasted until 2011. He also dated Camila Morrone from 2017 to 2022. The actor/film producer is reportedly romantically involved with Gigi Hadid.

Who is Tom Brady currently dating?

The seven-time Super Bowl winner was rumored to be romantically connected with Kim Kardashian. The socialite reportedly turned to Brady for real estate investing advice in purchasing a property in the Bahamas. However, the speculation couldn’t be verified.

Meanwhile, there were reports that model Irina Shayk followed Brady during Nahmad and Headrick’s wedding.

An insider told Page Six:

“She followed him around all weekend. She was throwing herself at him.”

But the three-time NFL Most Valuable Player isn’t interested in having a romantic relationship with Shayk.

Whatever Brady does next, playing football isn’t an option. ESPN’s Jenna Laine reported that Brady had already filed his retirement papers, bidding farewell to quarterback duties for good.

However, he may remain involved in the NFL after he reportedly bought a minority ownership stake with the Las Vegas Raiders. Tom Brady is also a part-owner of the WNBA’s Las Vegas Aces, which Kelsey Plum initially considered a joke.