Joshua Goldman
Joshua Goldman
min read · October 2, 2025 · Entertainment

Leonardo DiCaprio & Tobey Maguire: A Bond That Time Can't Diminish

Leonardo DiCaprio reunited with his longtime pal Tobey Maguire in Venice Beach for a stroll on Wednesday

Leo's Love Life Exposed: DiCaprio Spotted with Pals in Venice Beach Amid Fashion Week Chaos

The 50-year-old heartthrob has been making headlines for his high-profile relationships, but it seems he's taking a break from romance to spend quality time with his longtime buddy Tobey Maguire. The two Hollywood stars were spotted enjoying a low-key day out in Venice Beach on Wednesday, and we've got all the juicy details.

According to eyewitnesses, Leonardo DiCaprio was seen donning a simple yet stylish outfit, consisting of a black top, beige trousers, and white trainers. He completed his look with a black baseball cap and shielded his eyes with sleek black sunglasses. Tobey Maguire, on the other hand, opted for a more relaxed vibe in a black top paired with comfy joggers and grey trainers.

The Titanic actor and the Spider-Man star, both 50, enjoyed a day out together while Leonardo's model girlfriend, Vittoria Ceretti, is in Paris for Fashion Week

The duo's outing comes as Leo's model girlfriend, Vittoria Ceretti, is busy slaying the fashion scene in Paris for Fashion Week. The 25-year-old Italian beauty has been making waves on the catwalk and red carpet, and we can't help but wonder if she's feeling a little left out of the fun.

Sources close to the couple have revealed that Vittoria and Leo first sparked romance rumors back in August 2023 during an ice cream date in Santa Barbara. The two were then seen together at Milan Fashion Week the following month, and it seemed like their relationship was going strong.

However, things took a surprising turn when Vittoria hinted that she's tired of being labeled as "Leo's girlfriend." In an interview with Vogue France, she sidestepped using his name and referred to him as a "very, very famous movie star," citing his iconic role in Titanic. She also opened up about the importance of maintaining her independence and not letting labels define their relationship.

The duo, who have been pals for over 30 years, appeared in good spirits, laughing as they greeted each other

But what about all those rumors surrounding Leo's alleged preferences for younger models? It seems he's been linked to a string of beauties, including Camila Morrone, Gigi Hadid, and Blake Lively, all of whom are significantly younger than him. When asked about his dating habits in an interview with Esquire UK, DiCaprio confessed that turning 50 has made him realize the importance of honesty and openness in relationships.

"I have to be much more upfront," he revealed. "It's almost a responsibility because much more of your life is behind you than it is ahead of you." He also acknowledged that sometimes being blunt about what he wants can lead to relationships falling apart, but he insists he's not interested in wasting any more time on superficial connections.

But just last month, the couple was spotted enjoying a romantic dinner in West Hollywood as they celebrated their second anniversary. Vittoria even shared a photo of herself wearing a ring on her wedding finger, sparking engagement rumors. However, sources have since squashed those claims, insisting that Leo and Vittoria are not engaged.

For the occasion, Leonardo opted for a simple black top, beige trousers, and white trainers

So what's really going on behind closed doors? Is DiCaprio finally willing to settle down with someone his own age, or is he still chasing younger models? We'll be keeping a close eye on these developments as they unfold. Meanwhile, let's take a look at some of the most revealing quotes from Leo's interview:

"Turning 50 creates a feeling like you have a desire to just be more honest and not waste your time. I can only imagine how the next few decades are going to progress." - Leonardo DiCaprio

"Being more upfront and risking having things fall apart or risking the disagreements or risking going your separate ways from any type of relationship in life... You have to just be much more upfront. It's almost a responsibility, because much more of your life is behind you than it is ahead of you."

Leonardo's outing comes as his girlfriend joined a slew of stars in Paris for this year's Fashion Week

It seems like Leo is finally ready to open up and share his true feelings about love and relationships. But will he find someone who can keep up with his candid nature? Only time will tell.

UPDATE: We spoke with a source close to the couple, who revealed that Leo is indeed looking for something more mature in his relationship department. "He's had enough of being linked to young models," they told us. "He wants to ditch this image once and for all."

As for Vittoria, it seems she's not bothered by the constant attention from the media. In an interview with The Scholarly Note (thescholarlynote.com), she opened up about her relationship with Leo, saying: "It's something you learn. If what you're experiencing is real, if you know you love each other, then there's no reason to be alarmed. Because love protects and gives confidence."

Stay tuned for more updates on this exciting celebrity romance!