Tobey Maguire's Complete Dating History

Tobey Maguire's dating history is as impressive and colorful as his Hollywood career. The "Spider-Man" actor has been linked to numerous famous women over the years.

Tobey Maguire became a household name following the success of the 2002 "Spider-Man" film, where he plays the lead role. Portraying Peter Parker and Spider-Man in the "Spider-Man" trilogy cemented his status as a leading man in Hollywood.

Maguire has received critical acclaim for his performances and has won numerous awards throughout his career. In addition to his stellar acting career, Maguire is known for his high-profile romantic relationships.

Rashida Jones

Rashida Jones, the daughter of well-known record producer and musician Quincy Jones, was Maguire's girlfriend for three years. She reportedly began dating the handsome actor in 1997.

During that time, Jones was not as well known as Maguire, who had already achieved success in several movies from the late 1990s and the early 2000s, including "The Cider House Rules," "Pleasantville," and "Wonder Boys."

Maguire's celebrity seemed to outstrip his and Jones' romance, as most fans and even the show business press were far more interested in the actor's famous industry acquaintances, including fellow actor Leonardo Di Caprio.

Despite not being as well-known as a pair, Jones and Maguire were rumored to be engaged once. However, neither of them ever commented on the speculation. The couple reportedly split in 2000.

Jones moved on from their relationship and has found success her way. She became a breakout star in the hit NBC series "The Office," where she famously played the character Karen Filippelli.

In addition to showing off her excellent acting skills, Maguire's ex-girlfriend has also accomplished impressive feats as a producer, director, and writer.

Kirsten Dunst

One of Maguire's most publicized relationships was with Kirsten Dunst, a talented actress, singer, and model who has gained widespread recognition for her roles in several notable films and TV shows.

The two met on the set of the "Spider-Man" franchise in 2001, where he played Peter Parker, and she portrayed Mary Jane. The former's couple's "upside-down kiss" scene in the first "Spider-Man" film became an iconic moment in pop culture and won Best Kiss at the MTV Movie Awards in 2003.

However, both actors later revealed that the kiss was not as romantic as it appeared on screen due to technical difficulties. Despite their high-profile status and the public interest in their relationship, they managed to keep their romance as private as possible.

They were together for over a year before calling it quits in 2002. Despite the breakup, they remained cordial and even went on to film a second "Spider-Man" movie together.

Their relationship was a memorable part of the "Spider-Man" franchise, and their on-screen chemistry was highly praised by fans and critics alike. Like Maguire, Dunst's fame and success grew following the "Spider-Man" trilogy.

In 2011, Dunst received critical acclaim for her portrayal of a depressed newlywed in Lars von Trier's film "Melancholia," for which she won the Cannes Film Festival Award for Best Actress.

She also received nods from award-giving bodies for her roles in the FX series "Fargo," "Hidden Figures," "The Beguiled," "On Becoming a God in Central Florida," and most recently, "The Power of the Dog."

On "The Howard Stern Show," Howard Stern read a list of women Maguire was rumored to have been involved with– Kirsten Dunst, Demi Moore, Nicole Richie, and Christina Aguilera.

Jennifer Meyer

Maguire met Jennifer Meyer, a jewelry maker and entrepreneur, in 2003. They tied the knot in 2007 in a sunset ceremony in Kona, Hawaii, surrounded by a small group of family and friends, including Leonardo DiCaprio.

The couple, who welcomed their daughter Ruby nine months before their wedding, had kept their long-term romance on the down low. A close friend of Meyer's stated that the two had very reserved personalities.

But after nine years of marriage, Maguire and Meyer announced their separation in 2016. They already had two children at this time, having welcomed their son Otis in 2009. Their statement read:

"After much soul searching and consideration we have made the decision to separate as a couple."

The pair reportedly had difficulties in their marriage due to their conflicting lifestyles. Maguire preferred staying at home, while Meyer preferred going out and socializing. According to a source at the time, the couple "haven't seemed to be connecting" because of their differing interests.

The estranged couple lived apart shortly after announcing their separation. Despite their circumstances, Maguire continues to attend Meyer's jewelry launch parties.

Meyer expressed gratitude to her ex-husband for his endless support. She stated that she would not know what to do without him and described him as her "best friend."

Four years later, in 2020, Meyer filed for divorce from Maguire, though the couple has remained on friendly terms and supportive of one another. The actor even attended her jewelry launch in late 2017 and posed for photographs with her after their split.

Despite the couple's split, Meyer spoke highly of Maguire. On Father's Day in 2020, she shared a photo on Instagram and paid tribute to her ex-husband, calling him the "best daddy" to Otis and Ruby.

Meyer also described Maguire as her "baby daddy" and "greatest dad." The proud ex-wife added: "I'm sorry, Tobey, I know you hate Instagram, but every once in a while, I like to brag to everyone about how special you are."

There is little information available about Meyer's new relationship. However, in the same year she filed for divorce, she was reportedly dating sports agent Rich Paul. Later on, Paul started a relationship with English music superstar Adele.

Tatiana Dieteman

Maguire seemed to bounce back not long after his split from Meyer. In the summer of 2018, he was romantically linked to model Tatiana Dieteman, 17 years his junior. They were occasionally seen out and about together, although they kept their reported romance largely private.

Just before the COVID-19 lockdown, the pair were pictured together all loved up while holding hands in Los Angeles after having lunch at a vegan restaurant Crossroads Kitchen.

Maguire and Dieteman were in a relationship for approximately three years before splitting up. Not long after their breakup, Dieteman became romantically involved with famous surfer Koa Smith, with the couple confirming their relationship on Valentine's Day.

Dieteman had gone on a trip to Yosemite with some close friends, and she shared a sweet photo on Instagram that showed "The Ultimate Surfer" star with his arm around her.

On the other hand, Maguire was spotted with several women at different times, including one who followed him back to his home in Brentwood after a quick trip to the liquor store along with other friends.

It's unclear what caused the breakup between Maguire and Dieteman, but they have both moved on and are focusing on their lives and happiness.

The actor seemed to have immediately embraced his single life as he socialized with women, while Dieteman looked to have moved on as well, showing off her new romance.

Despite public interest in his dating life, Maguire has remained tight-lipped about his relationships. He seemed to prefer to keep his romance private and out of the public eye.

On "The Howard Stern Show," Howard Stern read a list of women Maguire was rumored to have been involved with– Demi Moore, Nicole Richie, and Christina Aguilera.

Maguire did not confirm or deny any of these names offered by Stern's show. His personal life may be the topic of rumors and speculation, but there's no denying the actor's talent and stature in the industry.

Maguire, a charismatic and sought-after leading man, joins many male celebrities in the entertainment industry who have repeatedly made headlines for captivating the hearts of beautiful stars.

Like Maguire, two of these dashing actors, Timothée Chalamet and Jason Segel, have been in the news recently because of their dating lives.

Chalamet dated actress Lily-Rose Depp and music legend Madonna's daughter Lourdes Leon. Similarly, Segel has his own dating history, reportedly dating actresses Lindsay Lohan and Michelle Williams.

Not much is known about Segel and Chalamet's new romantic partners, but one thing is sure about them, especially Maguire: their love lives have kept several tabloids busy.