Tobey Maguire was spotted sleeping with another much younger woman on Thursday, just a month after his ex-wife Jennifer Meyer announced their engagement.
The Spider-Man star, 49, walked down a New York City sidewalk with one arm around Danish model Mona Dugard, 22, and her girlfriend Vittoria Ceretti, 26.
The two seemed very friendly as they chatted during a low-key afternoon outing.
While grabbing a coffee to go, Tobey kept it super casual in jeans, a hoodie, a baseball cap, and Adidas sneakers.
Mona towered over the A-list actor as she sported a glamorous leather jacket, baggy jeans and walking shoes.
On Thursday, Tobey Maguire, 49, was seen flirting with Danish model Mona Dugard, 22, who is best friends with his friend Leonardo DiCaprio's girlfriend, Vittoria Ceretti, 26.
The model appeared without makeup, wearing her blonde hair in a bun and designer shadow over her eyes.
She was carrying a red shopping bag and then posted to her Instagram story with even more bags, saying the two went shopping.
Toby and Mona were joined by several of their friends, including Roseanne star Sarah Gilbert.
Ranked in the top 50 on models.com, Mona is a force to be reckoned with in the fashion world.
She was discovered at age 12 and three years later, at age 15, she was crowned the winner of the Elite Model Look Denmark.
She is currently signed to Elite Model Management.
The 5ft 10in beauty has starred in major fashion campaigns for brands such as Chanel, Marc Jacobs, Alaia, Bottega Veneta, Louis Vuitton and Versace.
Mona was only 18 years old when she landed her first Vogue cover.
She has since appeared on the covers of Vogue Japan, British Vogue, Korean Vogue, and French Vogue.
Mona has dominated catwalks around the world since her debut for Prada in 2019.
The two looked very friendly during the low-key afternoon outing with several friends, including Roseanne star Sarah Gilbert.
She was carrying a red shopping bag and then posted on her Instagram story with even more bags, saying that she and Tobi went shopping together.
Ranked in the top 50 on models.com, Mona is a force to be reckoned with in the fashion world; Seen in September 2024
Most recently, Mona attended the Gucci Spring Summer 2025 show during Milan Fashion Week in September.
Joining the catwalk was none other than her model best friend Vittoria Ceretti.
In addition to being close friends, she and the 26-year-old Italian beauty have worked together several times over the years.
They walked together in 2022 and 2023 and recently starred in Tory Burch's fall-winter 2024 campaign.
Vittoria has been dating Oscar winner Leonardo DiCaprio since August 2023.
Mona is the latest up-and-coming model to find herself in the arms of Hollywood lothario Toby.
The 49-year-old, who will turn 50 next June, was linked to the young women who were vacationing in Europe and New York City over the summer.
He was first rumored to be dating model Lily C, 20, after they were photographed together at billionaire Michael Rubin's star-studded Fourth of July white party in the Hamptons.
At that moment, Toby was seen leaving the party with Lily, and his hand appeared to brush her back.
Mona and her best friend Vittoria have walked countless runways together and recently starred in Tory Burch's Fall-Winter 2024 campaign; Seen in September 2024
Mona and Vittoria often post together on Instagram while traveling the world modeling.
Vittoria has been dating Tobey's best friend, Leonardo DiCaprio, 49, since August 2023; Seen in 2024
Lily has been working as a model since she was discovered at the age of nine and has recently been expanding her range into acting roles. He is also a popular YouTuber with 1.5 million followers on Instagram.
When photos of Toby and Lily surfaced, she faced backlash online for dating someone three years older than her 17-year-old daughter.
But his ex-wife Jennifer Meyer was quick to come to his defense, saying she and Chee were “just friends” and helped him “kindly” outside the party.
Three weeks later, Toby was seen with model actress Tara Louise Wagner.
The couple of different ages was photographed meeting at a pizzeria on July 24 in Saint-Tropez, France.
Tara has over 23.2k followers on her Instagram account, which is called @taralouwa, and her social media account lists her credentials as a “certified actress” and a “signed model” by the 2M agency. A portfolio of films listed under your name.
The following month, Toby was photographed with bikini model Babette Strijbos, 24, during a trip to Sardinia with his friend Leonardo and his girlfriend Vittoria.
Before dating Mona, Toby was rumored to be dating 20-year-old Lily C in the summer of 2024.
In July, he was seen on a date with model actress Tara Louise Wagner in France.
In August, Toby was photographed with bikini model Babette Strijbos, 24 (pictured).
Photos obtained by DailyMail.com show the couple barely able to keep their hands off each other as they bathe in the water on a secluded stretch of a private beach in Porto Cervo.
The 5ft 10in blonde bombshell from Amsterdam, Netherlands, was featured in Vogue Japan.
Toby has fully embraced the single life since his ex Jennifer Meyer filed for divorce from the Pleasantville star in 2020.
The former couple, who first announced their separation in 2016, married in 2007 and share two children: daughter Ruby, 17, and son Otis, 15.
Toby and Jennifer have maintained a friendly co-parenting relationship since their separation.
And in 2022, Jennifer called her divorce from Tobey “the most beautiful experience.” [her] Life' is the world's first one-episode podcast.
Last month, the 47-year-old jewelry designer announced her engagement to billionaire heir Geoffrey Ogunlesi, 33, after a year of dating.
Toby was previously married to jewelry designer Jennifer Meyer, 47, from 2007 until their divorce in 2020; Seen in 2016
Last month, the mayor revealed her engagement to billionaire heir Geoffrey Ogunlesi, 33, after a year of dating.
She did so by sharing a sweet photo with Jeffrey.
In the image, her hand rested gently on his, and a dazzling engagement ring (he had chosen it himself) reflected light on her finger.
'Yeah!!!' The mother of two captioned the Instagram snap with a black heart emoji, an infinity symbol and a sparkling star emoji.
