Leonardo DiCaprio's New Bond With Sean Penn Leaves Tobey Maguire Feeling 'Frozen Out'

Tobey Maguire is reportedly reeling as longtime pal Leonardo DiCaprio grows closer to his One Battle After Another co-star Sean Penn. Sources say the Titanic actor and the Hollywood veteran have struck up a powerful new friendship since filming wrapped earlier this year in Los Angeles.

The two have been spotted enjoying what insiders describe as 'long boozy meals', leaving Maguire feeling completely excluded.

According to whispers in Hollywood, DiCaprio, 50, and Penn, 65, have been inseparable since promoting their thriller, often spending evenings in deep conversation over fine Italian food and wine.

But while their connection blossoms, those close to Maguire claim he's been left watching from the sidelines — a painful position for someone who's been one of DiCaprio's closest friends for decades.

Tobey Maguire 'Frozen Out' as Leo Grows Closer to Sean

'There is no mistaking the friendship Leo has forged with Sean over the last year and a half', an insider confides. 'Nor can you ignore how Tobey Maguire doesn't participate in this relationship at all, and he and Leo have been friends since they were little kids.'

Sources say Penn has 'demanded – and gotten – a lot of one-on-one time with Leo'. The pair reportedly enjoy 'long dinners, long conversations' and have bonded deeply 'over their mutual love of Italian cuisine'. Maguire, however, is said to be struggling to relate. The Spider-Man star has a strict vegetarian diet and reportedly doesn't share his friends' enthusiasm for food.

'Food just isn't his love language', the insider adds. 'It's bumming him out, big-time – but right now Leo's made his choice, and Tobey's not involved at all.'

Observers say DiCaprio never expected such a close connection with Penn, especially after they played bitter enemies in One Battle After Another. 'I'd say Leo is as surprised by this development as anybody', the insider continues. 'He had no expectation of bonding with Sean the way he has. But Sean is now firmly part of Leo's inner circle, and there's nothing Tobey can do about it!'

Friends of the trio say Maguire has noticed the shift and feels the impact of being sidelined. DiCaprio and Maguire have been tight since their teenage years, often attending Hollywood events together. But now, the dynamic seems to have changed, and DiCaprio's new friendship with Penn appears to have taken centre stage.

Leo Reportedly Freezes Out Bradley — and Tobey May Be Next

This isn't the first time Leonardo DiCaprio's social circle has faced upheaval. As previously reported, DiCaprio allegedly distanced himself from friend Bradley Cooper after the Hangover star started dating his ex-girlfriend, Gigi Hadid.

Now, insiders say Maguire may also be feeling the chill. 'Sean and Leo have known each other casually for many years and had a major mutual pal in Robert De Niro', the source spills. 'But 2024 was the year they finally became bros, and that's crowded out Tobey, who is a hard guy to get along with under the best of circumstances.'

The insider adds that DiCaprio's growing friendship with Penn has completely shifted the balance in his inner circle. What began as a professional collaboration has become one of Hollywood's most talked-about bonds — and it seems Maguire, 50, has found himself on the outside looking in.