Emily Osment's Dating History, Young Disney Romance With Nathan Keyes, To Divorcing Jack Anthony

Emily Osment has spent much of her life in the spotlight. Rising to fame as ‘Lilly Truscott’, 'Hannah Montana’s' quirky best friend, she quickly became a household name for Disney Channel fans. While her acting and singing career have kept her busy for decades, her personal life, particularly her romantic relationships, has always had fans’ speculating.

Unlike some of her peers who embraced the limelight in their dating lives, Emily has often kept things private. Still, throughout the years, she’s been linked to several co-stars, musicians, and fellow actors, each relationship shaping her Hollywood journey. From young Hollywood flings to a whirlwind marriage and divorce, here’s a look at Emily Osment’s dating and relationship history.

Daryl Sabara and Emily Osment’s childhood romance

Emily Osment’s first public romance dates back to the early 2000s. In 2002, she was briefly linked to actor, Daryl Sabara, best known for playing ‘Juni Cortez’ in the Spy Kids franchise. The two reportedly met at a movie premiere, sparking a short-lived romance that captured fans’ attention. Despite the split, Emily and Daryl remained on good terms and continued to support each other’s careers. Daryl later went on to marry singer, Meghan Trainor in 2018, while Emily’s love life was just beginning to unfold.

Mitchel Musso and Emily Osment went from on-screen friends to real-life dating

By 2008, Emily was one of the most recognisable Disney Channel stars thanks to Hannah Montana. It was during this period that she was rumoured to be dating her co-star, Mitchel Musso, who played ‘Oliver Oken’ on the show. Their chemistry on-screen carried over into real life, with the two reportedly dating for a few months. However, the relationship didn’t last long, and they decided to remain friends. 

Emily Osment was linked with Tony Oller

Emily’s next romance blossomed on another Disney set. In 2009, she began dating Tony Oller, her co-star from As the Bell Rings. Their on-screen connection turned into real-life romance, and the couple often appeared together at events, showcasing their love. However, as it happens with many teen Hollywood romances, their relationship was short-lived. By 2010, the pair had gone their separate ways. Tony eventually found fame as one-half of the pop duo MKTO, while Emily focused on her acting and music career.

Emily Osment and Nathan Keyes had a brief but impactful relationship

In 2012, Emily began dating actor, Nathan Keyes, known for films like The Kings of Summer and Ben 10: Alien Swarm. The two reportedly met while working on a project and quickly grew close. For a time, they shared sweet moments on social media, giving fans a glimpse into their relationship. However, their romance was short-lived, ending in early 2013. Though brief, this relationship marked Emily’s shift from Disney Channel romances to more serious Hollywood relationships.

Emily Osment and her connection with Jimmy Tatro

Following her breakup with Nathan, Emily started dating Jimmy Tatro in 2013. At the time, Jimmy was best known for his YouTube channel Life According To Jimmy, where he built a massive following with his comedy sketches. The couple met at a party and quickly connected over their shared sense of humor. They attended events together and often appeared in each other’s social circles. However, their relationship ended in late 2014. 

Emily Osment and her relationship with Jim Gilbert

Emily’s most stable and longest relationship came in late 2015, when she began dating Jim Gilbert, a fitness trainer and entrepreneur. Unlike her previous romances, Emily and Jim kept their relationship relatively low-key, sharing only occasional glimpses of their life together on social media. For four years, the couple supported each other’s careers, with Emily diving deeper into acting projects like Young & Hungry and Jim focusing on his Los Angeles-based fitness business.

Despite the privacy they maintained, fans could see the happiness and love they shared. By 2019, the couple quietly ended their relationship. The breakup was amicable, but it marked the end of Emily’s longest and most serious romance at the time.

Emily osment and Jack Anthony’s whirlwind romance and divorce

Emily’s next relationship would prove to be her most publicised and ultimately, her most heartbreaking one. In late 2021, she was spotted with Jack Anthony (real name Jack Farina), a musician and producer. The couple confirmed their relationship in early 2022 when Emily posted Valentine’s Day pictures on Instagram, calling him her 'valentine'.

Their romance seemed strong with the pair vacationing in Hawaii and Canada, and making red carpet appearances together. In October 2024, Emily and Jack tied the knot in a romantic wedding, marking a new chapter of happiness for the Hannah Montana star.

Unfortunately, their marriage ended almost as quickly as it began. Court documents revealed that the couple separated less than two months after the wedding. By March 2025, Emily filed for divorce, citing 'irreconcilable differences'. Reports also confirmed that a prenuptial agreement had been in place. On September 8, 2025, a judge finalised their divorce, just few months after they first said 'I do.' Emily released a statement reflecting on the split, she wrote:

“I think with any big decision in your life, whether it’s relationships or work or whatever it may be, you have to firmly plant both feet in that decision. Ultimately, it didn’t work out.”

The abrupt end of their marriage shocked fans, especially given how happy the couple appeared in public. Nonetheless, Emily has remained poised and focused on her career, appearing at major events like the 2025 CBS Fest shortly after the news broke.

Now officially single, Emily continues to balance her career as an actress and singer while navigating life’s ups and downs. Fans remain supportive, eager to see what’s next for her both professionally and personally.

Also Read: Ryan Seacrest, Hollywood's Famous Host: Depressed To Be Single At 50, Dated Five Women In 16 Years

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