Tobey Maguire and Jennifer Meyer split up in 2016. Their divorce was pretty quiet, and it didn’t seem like there was a huge fight over assets or custody. Everything seems pretty amicable in general. Tobey had a much-younger girlfriend a few years after his divorce, but I don’t think they’re together anymore. It seems like Tobey is single right now and looking to pick up some young lady. His pick-up lines must be pretty rusty though: “Y’all remember Seabiscuit?” and “I was Spider-Man too for a while.” So Tobey’s BFF Leonardo DiCaprio decided to help out his bro, and one of the founding members of the P-ssy Posse. Leo went out as Tobey’s wingman last week! The results were… not good.
Old pals Leonardo DiCaprio and Tobey Maguire were spotted partying together in the VIP section of nightclub MainRō restaurant and supper club in Hollywood on Thursday night.
“Tobey and Leo came to the club together for a boys’ night out,” a source tells Page Six. “It was very clear that Tobey was on the prowl and Leo was his wingman. Leo introduced Tobey to three different blondes.”
But it seems that even starring in the latest “Spider-Man” installment doesn’t attract the ladies.
“Even with Leo’s help, Tobey couldn’t land a girl,” the source continued. “None of them seemed interested when introduced.”
The duo arrived at 10.30 p.m. but called defeat less than two hours later, leaving, “because it was clear they were having no luck.”
DiCaprio, 47, and Maguire, 46, have been friends for decades and were part of a notorious group of thespian pals that dubbed themselves the “p—y posse.” Other members included Lukas Haas, Kevin Connolly and David Blaine.
Thanks, I want this to be a Hollywood movie? I want Tobey and Leo to star in a movie, documentary style, of Leo going around a nightclub, introducing himself to random 20-something blondes, bringing those blondes back to Tobey and the blondes completely blanking him. I’m laughing just thinking about it. Maybe the movie could be shown through the blondes’ perspectives. And is Tobey’s “type” really “young blonde”? That’s Leo’s type. I think Tobey would be fine with dating women over the age of 25, and women with dark hair or red hair. But who knows. Another P-ssy Posse adventure ends in tragedy!! I love that 47-year-old Leo – arguably one of the most in-demand actors in the world – is doing wingman sh-t for his bro. Leo probably loved it though. I bet he relishes spending time with Single and Ready to Mingle Tobey.
Photos courtesy of Instar, Avalon Red.
May 15, 2013: Leonardo DiCaprio, Tobey Maguire attending the Opening Ceremony and ‘The Great Gatsby’ Premiere during the 66th Annual Cannes Film Festival at the Theatre Lumiere today in Cannes, France. Mandatory Credit: INFphoto.com Ref: inffr-09/nEditorial Rights Managed Image ? Please contact www.INSTARimages.com for licensing feeby phone at 212-414-0207 or email sales@instarimages.com – Image or video may not be published in any way that is or might be deemed defamatory, libelous, pornographic, or obscene / Please consult our sales department for any clarification or question you may have – http://www.INSTARimages.com reserves the right to pursue unauthorized users of this image r video. If you violate our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image or video, and where appropriate, the cost of collection and/or statutory damage. 
96572, CANNES, FRANCE – Wednesday May 15, 2013. Tobey Maguire, Carey Mulligan and Leonardo DiCaprio attend the photocall for ‘The Great Gatsby’ at The 66th Annual Cannes Film Festival at Palais des in Cannes. **NORTH AMERICA ONLY** Photograph: © Optic Photos, PacificCoastNews.com **FEE MUST BE AGREED PRIOR TO USAGE** **E-TABLET/IPAD & MOBILE PHONE APP PUBLISHING REQUIRES ADDITIONAL FEES** LOS ANGELES OFFICE: +1 310 822 0419 LONDON OFFICE: +44 20 8090 4079,Image: 527633259, License: Rights-managed, Restrictions: WORLD RIGHTS, DIRECT SALES ONLY UNLESS STATED OTHERWISE IN CAPTION – Fee Payable Upon Reproduction – For queries contact Avalon.red – sales@avalon.red London: +44 (0) 20 7421 6000 Los Angeles: +1 (310) 822 0419 Berlin: +49 (0) 30 76 212 251 Madrid: +34 91 533 4289, Model Release: no, Credit line: Optic Photos, PacificCoastNews.c / Avalon 
96572, CANNES, FRANCE – Wednesday May 15, 2013. Tobey Maguire, Carey Mulligan and Leonardo DiCaprio attend the photocall for ‘The Great Gatsby’ at The 66th Annual Cannes Film Festival at Palais des in Cannes. **NORTH AMERICA ONLY** Photograph: © Optic Photos, PacificCoastNews.com **FEE MUST BE AGREED PRIOR TO USAGE** **E-TABLET/IPAD & MOBILE PHONE APP PUBLISHING REQUIRES ADDITIONAL FEES** LOS ANGELES OFFICE: +1 310 822 0419 LONDON OFFICE: +44 20 8090 4079,Image: 527633260, License: Rights-managed, Restrictions: WORLD RIGHTS, DIRECT SALES ONLY UNLESS STATED OTHERWISE IN CAPTION – Fee Payable Upon Reproduction – For queries contact Avalon.red – sales@avalon.red London: +44 (0) 20 7421 6000 Los Angeles: +1 (310) 822 0419 Berlin: +49 (0) 30 76 212 251 Madrid: +34 91 533 4289, Model Release: no, Credit line: Optic Photos, PacificCoastNews.c / Avalon
96690, CANNES, FRANCE – Wednesday May 15, 2013. Amitabh Bachchan, Carey Mulligan, Tobey Maguire and Leonardo DiCaprio attend the opening ceremony for the 66th Annual Cannes Film Festival in Cannes. Opening night featured a screening of ‘The Great Gatsby.’ **NORTH AMERICAN USE ONLY** Photograph: © Kika Press, PacificCoastNews.com **FEE MUST BE AGREED PRIOR TO USAGE** **E-TABLET/IPAD & MOBILE PHONE APP PUBLISHING REQUIRES ADDITIONAL FEES** LOS ANGELES OFFICE: +1 310 822 0419 LONDON OFFICE: +44 20 8090 4079,Image: 528165509, License: Rights-managed, Restrictions: WORLD RIGHTS, DIRECT SALES ONLY UNLESS STATED OTHERWISE IN CAPTION – Fee Payable Upon Reproduction – For queries contact Avalon.red – sales@avalon.red London: +44 (0) 20 7421 6000 Los Angeles: +1 (310) 822 0419 Berlin: +49 (0) 30 76 212 251 Madrid: +34 91 533 4289, Model Release: no, Credit line: Kika Press, PacificCoastNews.com / AvalonncG1vNJzZmivp6x7pLHLnpmirJOdxm%2BvzqZmcG1jboB0e8ueppicmZiusb7IqJatqpmasaDAzpiZnpekpK%2Bmxb6mmKCtmaeytKvWoqWgpZGjrKLAvpqWnKSll6yjwdOYq6Gdj5y2s7jSmJmlmZ6gsqWr06iZnrFf