Tobey Maguire struggles to land a woman, even with Leonardo DiCaprio as a wingman

Leo and Tobey
Tobey Maguire had trouble landing a girl, even with Leonardo DiCaprio’s help. ©

As it turns out, even top Hollywood actors can strike out.

Tobey Maguire appeared to have trouble landing a girl even with Leonardo DiCaprio serving as a wingman.

Tobey and Leonardo partied in Los Angeles this week, hanging out at MainRō on Thursday night and The Nice Guy on Friday night.

Hollywood is the place to be this weekend. Super Bowl LVI has attracted the likes of athletes, actors, and musicians. The Los Angeles Rams will represent the city in the sports spectacle, and pre-Super Bowl festivities are in full swing, in anticipation of the big game.

The actors chatted it up with the ladies and enjoyed the nightlife. The Don’t Look Up actor did his best to introduce the Spiderman actor to women, but he did not have much luck.

Tobey Maguire couldn’t land a girl, even with the help of Leonardo DiCaprio

Tobey Maguire couldn’t land a girl, even with Hollywood heartthrob Leonardo DiCaprio by his side. On Thursday, the two celebrated a boys’ night out in the VIP section of MainRō supper and nightclub in Hollywood. 

According to sources, it was clear that Tobey was “on the prowl.”

Leonardo introduced Tobey to at least three blondes, but had no luck. The source added, “Even with Leo’s help, Tobey couldn’t land a girl. None of them seemed interested when introduced.”

DiCaprio and Maguire arrived at MainRō at 10:00 p.m. and left two hours later, without any ladies accompanying them.

Tobey Maguire and Leonardo DiCaprio were at Hollywood hotspot The Nice Guy Friday night for an afterparty for Justin Bieber. Later in the night, shots rang out, with four people injured

There is no word if Maguire had better luck with the ladies last night.

The actor met Jennifer Meyer on the set of Seabiscuit, and the former lovers married in 2007. The two share a daughter Ruby, 15, and a son, Otis, 12.

Leonardo DiCaprio and Tobey Maguire’s friendship

Tobey and Leonardo are longtime pals; the two started their acting careers in Hollywood around the same time. The actors have worked together in movies like The Great Gatsby and This Boy’s Life.

Leonardo and Tobey became friends when DiCaprio was 12. Leonardo recounted driving with his mother, “I literally jumped out of the car. I was like, ‘Tobey! Tobey! Hey! Hey!’ And he was like, ‘Oh, yeah — I know you. You’re… that guy.’ But I just made him my pal. When I want someone to be my friend, I just make them my friend.”

DiCaprio may not be a great wingman, but he certainly has confidence.

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