Entertainment Books Biographies Elon Musk Pursued Grimes with Wild Autopilot Ride on Date, Book Says: 'Covered His Eyes' Walter Isaacson's biography of the X owner reveals how he wooed Canadian singer Grimes by showing off his Tesla's Autopilot feature By Nikki Dobrin Nikki Dobrin Nikki Dobrin has more than 20 years of international experience working in media and entertainment. She joined the PEOPLE team in 2023 and currently serves as a Writer/Editor. People Editorial Guidelines Published on August 9, 2023 12:09AM EDT Grimes first dinner date with Elon Musk involved a thrilling joyride, according to Musk's biographer. Photo: getty (2) Elon Musk tried hard to impress singer Grimes when they began dating by driving his Tesla hands-free and with eyes covered, according to excerpts from Walter Isaacson's new biography on the Tesla CEO. During their second date in 2018, Musk, 52, took his hands off the steering wheel and covered his eyes with them, in an attempt to show off his car's Autopilot feature and how fast it accelerated, Isaacson wrote. “While driving her to a restaurant, he showed how fast the car accelerated, then took his hands off the wheel, covered his eyes, and let her experience Autopilot,” Isaacson wrote in a passage the author shared on X, formerly known as Twitter. “I was like, oh s---, this guy is f---ing crazy,” Grimes, 35, told Isaacson. "The car was signaling and changing lanes by itself. It felt like a scene out of a Marvel movie.” Tesla does not advise drivers to operate its vehicles in this way, according to the Model Y Owner's manual. The "cabin camera can determine driver inattentiveness and provide you with audible alerts, to remind you to keep your eyes on the road when Autopilot is engaged," the manual reads. Elon Musk and Grimes' Relationship: A Look Back According to Isaacson, Musk and Grimes connected on social media in 2018 when the SpaceX CEO asked the "spellbinding performing artist" out to dinner, which began their three-year romance. Following his split from actress Amber Heard, Musk reached out to Grimes on Twitter, after enjoying a shared pun related to the concept of Roko’s basilisk, a thought experiment that proposes a future in which a malignant artificial intelligence will rise up and seek to punish those who did not aid in its creation and do its bidding, Isaacson wrote. The two enjoyed their first date after Musk invited Grimes to fly to his Tesla factory in Fremont, California, where “we just walked the floor all night, and I watched him try to fix things,” Grimes told Isaacson. The following night, the mogul picked up the "Oblivion" singer for dinner and took her on the thrilling joyride in his Tesla. Elon Musk's Dating History: From Amber Heard to Grimes Never miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories. During the date, the author writes that when Grimes compared Musk to Gandalf the powerful wizard from The Lord of the Rings, he tested her knowledge of the epic fantasy series by giving her a "rapid-fire" trivia test, which she passed. “That mattered to me,” Musk told Isaacson. Grimes, whose legal name is Claire Elise Boucher, later gave Musk a box of animal bones she collected as a gift. "And thus into Musk’s life in the spring of 2018, amid the emotional tsunami caused by his breakup with Amber Heard, came a waiflike weaver of sounds, Claire Boucher, known as Grimes, a smart and spellbinding performance artist whose appearance would lead to new children, on-and-off domesticity, and even a public battle with an unhinged rapper," Isaacson wrote of the start of the relationship. Grimes responded to Isaacson's excerpt on X, writing, "Your prose is beautiful walter." Musk and Grimes dated off and on for three years. Grimes gave birth to their first child, a son named X Æ A-XII, nicknamed "X," in 2020. In December 2021, they welcomed their daughter Exa Dark Sideræl, whom they nicknamed "Y," via surrogate. Grimes Says Her Son 'Can Sense My Distaste for the Word Mother' and Calls Her By Her First Name After their daughter was born, Grimes announced the end of their relationship. "Me and E have broken up *again* ... but he’s my best friend and the love of my life, and my life and art are forever dedicated to The Mission now," she posted on Twitter in 2021. In addition to his two children with Grimes, Musk shares 19-year-old twins Vivian Jenna Wilson and Griffin Musk; and triplets Kai, Damian and Saxon Musk, who were born in 2006, with his first wife, Justine Wilson. The two had another son, Nevada Musk, who died at 10 weeks. Musk and venture capitalist Shivon Zilis welcomed twins via surrogate in November 2021. Simon & Schuster's Elon Musk by Walter Isaacson is due out Sept. 12, and is available for pre-order now, Close