Emily Osment’s Dating History: From Young Disney Romances to Recent Heartbreak
Emily Osment, the former child star who rose to fame as Miley Cyrus’s quirky best friend Lilly Truscott on Hannah Montana (2006–2011), has navigated a career blending Disney innocence with mature roles in shows like Young & Hungry and Young Sheldon. Born in 1992, Osment’s early Disney days often overlapped with her personal life, leading to several high-profile romances with fellow young stars. At just 33, her dating history reflects the whirlwind of Hollywood youth, from co-star crushes to more private adult relationships. Below, we break down her known romantic timeline, drawing from public sightings, interviews, and social media hints.
Early Disney Days: Co-Star Sparks and Teenage Flings (2007–2010)
Osment’s Disney era was as much about on-screen chemistry as off-screen buzz. Her first major public romance came with a Hannah Montana co-star, setting the tone for her young Hollywood love life.
- Mitchel Musso (2007–2009): Osment’s breakout romance was with her Hannah Montana on-screen crush, Oliver Oken (played by Musso). The pair dated for nearly two years, starting around 2007 when they were both teens. Fans shipped them hard, but the relationship ended amicably amid busy filming schedules. Musso later reflected on it fondly, noting their young age made it “innocent and fun.” This Disney duo exemplified the network’s tendency for real-life pairings.
- Tony Oller (2009–2010): Fresh off her Musso split, Osment was spotted with As the Bell Rings actor Tony Oller at a Dodgers game in late 2009. Their brief, PDA-filled romance lasted about eight months, fueled by shared Disney connections—Oller appeared in short-form series on the network. Paparazzi photos captured their hand-holding dates, but they parted ways quietly in 2010, likely due to youthful timing.
These early flings highlighted the “Disney dating pool,” where co-stars like Osment and Oller bonded over the pressures of child stardom.
Post-Disney Romances: Hollywood Peers and YouTube Stars (2011–2015)
As Osment transitioned to edgier roles in films like Cyberbully (2011), her love life mirrored her maturing image, blending actors and rising online influencers.
- Daryl Sabara (Rumored, 2002–2003): One of Osment’s earliest rumored links was with Spy Kids co-star Daryl Sabara (now Meghan Trainor’s husband). At ages 10 and 11, they shared innocent crushes during filming, but no confirmed dating—just sweet, unverified whispers of puppy love.
- Nathan Keyes (2013–2014): Osment’s longest early relationship was with actor Nathan Keyes (The Kings of Summer), starting in January 2013. The pair, both Disney alums (Keyes in Hannah Montana: The Movie), dated for about 18 months, sharing holidays and red-carpet moments. They split in September 2014 but remained friends—Keyes even posted a throwback photo in 2020, captioning it nostalgically.
- Jimmy Tatro (2013–2015): Overlapping briefly with Keyes (rumors suggest an on-off dynamic), Osment dated YouTuber and actor Jimmy Tatro from October 2013 to March 2015. The 22 Jump Street star, known for his comedy sketches, met Osment through mutual friends. They collaborated on short films like Fighting Couple and went public at events, but called it quits after about 18 months. Tatro later joked about their “drunk questions” series in interviews.
This period marked Osment’s shift from Disney kid to independent artist, with relationships reflecting her growing circle in comedy and online media.
Adult Relationships: Privacy, Engagements, and a Swift Divorce (2016–2025)
As Osment starred in Young & Hungry (2014–2018), she leaned into more private romances, often sharing glimpses on Instagram but shielding details. Her recent chapter has been a rollercoaster of commitment and separation.
- Jim Gilbert (2016–2019): Osment’s most stable pre-pandemic romance was with fitness enthusiast Jim Gilbert, starting in June 2016. The non-celebrity partner worked with the Verdugo Hills Autism Project, offering Osment a “normal” dynamic away from Hollywood. She gushed about him on Twitter and Instagram, calling him her “therapist boyfriend” in playful posts. They dated for three years before an amicable split in 2019, with Osment later praising the benefits of dating outside the industry.
- Jack Anthony (Farina) (2021–2025): Osment’s most recent and publicized relationship was with singer-songwriter Jack Anthony (real name Jack Farina), sparking rumors in late 2021 after hand-holding sightings. She went Instagram official on Valentine’s Day 2022, calling him her “valentine.” They got engaged in June 2023 during a Yosemite trip, with Osment sharing the ring on social media: “This love is so big.” The couple married privately on October 12, 2024, keeping it low-key amid Osment’s Young Sheldon finale buzz.
However, the fairy tale ended abruptly. Osment filed for divorce on March 7, 2025, citing irreconcilable differences, with their separation dated December 7, 2024—just two months post-wedding. The couple, who had a prenup and no children, has kept details private. Osment has not commented publicly, focusing on her career, including her role in the upcoming Pretty Smart reboot.
As of September 2025, Osment appears single, prioritizing her post-divorce healing and projects like voice work in The Kominsky Method.
Patterns and Insights: Disney’s Lasting Shadow on Love
Osment’s history shows a pattern: Early romances with Disney peers (Musso, Oller) gave way to more diverse partners (Tatro’s YouTube fame, Gilbert’s normalcy, Anthony’s music world). She’s often praised non-industry relationships for their grounding effect, telling outlets like Distractify in 2021 that they offer “cool benefits” like escaping the spotlight. Yet, her quick marriage and divorce with Anthony highlights the challenges of blending fame with personal milestones.
Public reactions to her splits have been supportive, with fans on X noting her resilience: “Emily deserves happiness after that whirlwind year.” As a former young Disney star, Osment’s story resonates with fans who grew up alongside her—proving that even off-screen, life’s plot twists keep coming.
For U.S. audiences, her journey mirrors broader celeb dating trends: From child-star hookups to seeking stability, all under tabloid scrutiny. With no new rumors as of September 2025, Osment seems focused on career wins, perhaps eyeing her next chapter wisely.