Elon Musk, the enigmatic billionaire behind Tesla, SpaceX, and X, is as renowned for his groundbreaking innovations as he is for his complex personal life. With a fortune estimated at over $250 billion and a mission to colonize Mars, Musk’s romantic history has captivated public attention, featuring a roster of high-profile women and a growing family of 14 children with four partners. From college sweethearts to Hollywood actresses and tech executives, Musk’s relationships have been marked by passion, turbulence, and an unconventional approach to love. As of May 12, 2025, the question lingers: among Justine Musk, Talulah Riley, Amber Heard, Grimes, Shivon Zilis, and Ashley St. Clair, who did he love the most? This article delves into his romantic past to explore the depth of these connections and the elusive answer to Musk’s heart.

The Early Years: Jennifer Gwynne and Justine Musk

Musk’s romantic journey began in the mid-1990s at the University of Pennsylvania, where he met Jennifer Gwynne, a fellow student drawn to his “quiet intensity.” Their year-long relationship was marked by small, thoughtful gestures—like a gold and emerald necklace Musk gifted her—before distance ended it. Gwynne’s fond memories, shared during a 2022 auction of their mementos, suggest a sweet but fleeting bond, unlikely to rank as Musk’s deepest love given its brevity.

His first marriage came with Justine Wilson, met at Queen’s University in Canada. Married in 2000, their union produced six children, though it was marred by tragedy with the loss of their firstborn, Nevada, to SIDS in 2002. Justine bore twins Griffin and Vivian, and triplets Kai, Saxon, and Damian through IVF, but their relationship deteriorated amid Musk’s growing ambition. Justine’s 2010 Marie Claire essay revealed a combative dynamic, with Musk asserting dominance and her feeling sidelined. Their 2008 divorce, despite shared custody, hints at a love that faded under pressure. Justine’s later reflections suggest respect but no lingering romance, positioning her as a significant but not ultimate love.

The Turbulent Marriages: Talulah Riley

Musk’s relationship with British actress Talulah Riley began in 2008, shortly after his divorce from Justine. Their whirlwind romance led to a 2010 marriage, but it unraveled by 2012, with Musk citing a lack of rekindled passion after a trial separation. Remarkably, they remarried in 2013, only to divorce again in 2016. Riley’s public statements—calling Musk kindhearted and noting their amicable post-divorce friendship—paint a picture of mutual affection. Yet, the repeated splits suggest a love more rooted in companionship than enduring passion. Without children, their bond, while intense at times, lacks the familial depth seen in other relationships, making it a contender but not the strongest.

The Hollywood Flame: Amber Heard

Musk’s brief but fiery romance with Amber Heard ignited in 2016, post her separation from Johnny Depp. Their year-long relationship, marked by public appearances and Heard meeting Musk’s children, ended in 2017 due to conflicting schedules. Musk’s Rolling Stone interview revealed the breakup’s emotional toll, calling it “hurt bad,” and he later praised their amicable split. A 2020 legal battle over frozen embryos hinted at deeper ties, but Heard’s testimony suggested a friendship rooted in shared intellectual curiosity rather than lifelong love. This passionate but short-lived affair, lacking the permanence of family, seems more a fling than Musk’s truest love.

The Artistic Muse: Grimes

Musk’s relationship with Canadian musician Grimes (Claire Boucher) stands out for its longevity and creativity. Starting in 2018 with a flirty Twitter exchange, they debuted at the Met Gala and welcomed three children: X Æ A-Xii (2020), Exa Dark Sideræl (2021), and Techno Mechanicus (2022), all via surrogate. Their on-off dynamic—splitting in 2021, reconciling, then parting again—reflects a fluid bond. Grimes’s 2022 Vanity Fair interview called Musk “the love of my life” and her “best friend,” despite their unconventional living arrangements. Her 2025 pleas for privacy amid public scrutiny of their children suggest a deep emotional investment. Musk’s frequent appearances with their son X Æ A-Xii and his role in their “Mission” (a term Grimes uses for their shared vision) indicate a profound connection, bolstered by creative and parental ties. This relationship’s complexity and duration make it a strong candidate for his greatest love.

The Professional Partner: Shivon Zilis

Musk’s relationship with Shivon Zilis, a Neuralink executive, is less romantic and more pragmatic. They welcomed twins Strider and Azure in 2021, followed by a third child, Arcadia, in 2024, and a fourth, Seldon Lycurgus, in 2025, all via IVF. Zilis’s 2025 X post celebrating Arcadia’s birthday and announcing Seldon portrays a warm co-parenting dynamic, but she frames it as professional, not romantic. Musk’s public silence on their personal status, contrasted with his active involvement with Grimes’s children, suggests a functional rather than passionate bond. With four children, their connection is significant, but its lack of publicized affection places it below others in emotional depth.

The Latest Chapter: Ashley St. Clair

The newest addition, conservative influencer Ashley St. Clair, claimed in February 2025 that Musk fathered her son Romulus in September 2024. Her X announcement, citing privacy concerns, and a custody filing for sole custody amid financial disputes (including a withdrawn $15 million offer) paint a contentious picture. Musk’s ambiguous response—“I don’t know if the child is mine”—and reduced support suggest distance. This nascent, conflict-ridden relationship lacks the history or warmth to rival his deeper connections, positioning it as the least likely to reflect his truest love.

Analyzing the Evidence: Who Did He Love Most?

Determining Musk’s greatest love requires weighing emotional intensity, duration, and familial bonds. Justine and Riley offered early stability and affection, but their relationships ended with mutual respect rather than lingering passion. Heard’s romance was intense but fleeting, lacking long-term commitment. Zilis and St. Clair represent practical or disputed partnerships, with limited emotional public evidence. Grimes, however, stands apart. Her decade-long on-off relationship, three children, and shared creative vision—evidenced by their “Mission” and Musk’s public displays with X Æ A-Xii—suggest a love that endures despite challenges. Musk’s own words, like his 2021 Page Six comment about remaining “on great terms” with Grimes, and her reciprocal devotion, reinforce this.

Yet, Musk’s private nature and pro-natalist stance—expressed in his 2022 tweet about combating the “underpopulation crisis”—complicate the narrative. His relationships often serve his vision of expanding humanity, suggesting love might intertwine with purpose. Grimes aligns most with this vision, sharing his eccentricity and futurism, while others reflect different phases or practical alliances. Without direct statements from Musk—unlikely given his guardedness—Grimes emerges as the strongest contender, her bond blending romance, family, and ideology in a way the others do not.

Conclusion

Elon Musk’s love life is a tapestry of high-profile romances, each leaving a mark on his personal and public identity. From Justine’s foundational role to Grimes’s enduring partnership, each woman contributed to his story. As of May 12, 2025, the evidence leans toward Grimes as the one he loved most, her decade-long presence and shared vision outlasting the others. Yet, Musk’s complex motivations—blending love with legacy—leave room for debate. His heart, like his ventures, remains a frontier yet to be fully explored.