Everything We Know About Emily Osment's Boyfriend and Ex-boyfriends

Emily Osment grew accustomed to the Hollywood spotlight from a young age, and as she grew older, fans took an interest in her dating life. The actress has been somewhat open about her romances, the former flames of which include both celebrities and non-celebrities.

Los Angeles native Emily Osment debuted her film and TV career, starring as Miranda Aiken in 1999's "The Secret Life of Girls" at seven years old. The comedy-drama opened more doors for the actress, as after appearing in the following walk-on roles in TV shows, she starred as Gerti Giggles in the cult-classic "Spy Kids" movie franchise.

The multi-talented star also took voice-acting gigs while building a musical career as a pop singer. She catapulted to worldwide renown when she starred as Lily, Miley Stewart's best friend, in the beloved kids' series "Hannah Montana." Osment's fanbase grew exponentially as she captured many hearts with her portrayal of Lily's silly and loveable nature.

Her fame thrust her personal life into the spotlight, leading curious fans to wonder about her dating history. At one point, those very supporters began suspecting she was dating her former "Hannah Montana" co-star Mitchell Musso. Though the two never addressed the speculation, it seems their romance never came to pass.

Still, Osment has had an active dating life and hasn't been afraid of celebrating her love for her former flames online. While she has dated other fellow actors, she found "cool" benefits to dating men who weren't in the industry. But even so, she has maintained the privacy of her relationships, never revealing their innermost details.

Jimmy Tatro Was Reportedly Emily Osment's Boyfriend in 2013

A few years before her romance with Jimmy Tatro began, Osment was linked to fellow Disney star Tony Oller in 2009. The pair reportedly had been spotted at several public events, often cozied up with each other. Although neither Oller nor Osment addressed the speculation, their relationship is said to have ended the following year.

Osment was then rumored to be dating actor Nathan Keyes. The ex-lovers kept their relationship relatively private, though they often appeared on other's social pages when they were still together. The timeline of their romance is also unclear, but it reportedly spanned over 18 months between 2010 and 2012.

Despite their separation, though, Osment and Keyes maintained a healthy bond. In August 2020, Keyes shared a photo of himself and the "Young Sheldon" star at the "Unintended" Premiere in New York City. He captioned the black-and-white picture, "New York looks like a dream to me now @emilyosment."

Osment then started dating Tatro. The pair had met through a mutual friend, and their relationship lasted between 2013 and 2015. Like with her former beaus, Osment appeared on Tatro's social pages, and the former couple walked several red carpets together.

They also collaborated as actors, such as on the film short "Fighting Couples" in 2013. Osment would also feature in Tatro's YouTube videos, such as the one titled "Drunk Questions." The reason for their split is unknown, but currently, Tatro is dating "Vampire Academy" actress Zoey Deutch.

Jim Gilbert Was Emily Osment's Boyfriend, Who Was Her 'Not-In-The-Industry' Guy

Osment's romance with Jim Gilbert began in the summer of 2016. They kept their relationship under wraps for the first several months. During that time, Osment gave subtle hints that she had found new love, including an October 2016 tweet about her "therapist boyfriend."

She eventually went public with the romance in 2017. During a chat with People that May, she revealed that Gilbert led a career outside of entertainment and explained the benefits that came with having a non-celebrity boyfriend, as she said:

"I've got a wonderful boyfriend who's not in the industry, which is great. [...] It's nice because he's in a completely different industry than I am, and we have so much to talk about anyway, and we get to come home and say, 'Oh, how was your day and how was your day?' And there's nothing in common, which is cool."

According to some outlets, Gilbert worked for the Verdugo Hills Autumn Project. This information was retrieved from his Facebook bio; however, he has since deactivated his account. Still, despite a seemingly non-existent social media presence, he appeared on Osment's Instagram in several posts.

That was until 2019 when the actress had removed all traces of him from her accounts. She spoke with Atwood Magazine that October, revealing that she was a single woman. Osment reveled in that relationship status as she reflected:

"I've been single for quite some time now – and it’s been so great! It’s nice to sort of give yourself that freedom and sort of grow on your own before you find someone new to grow with you."

Jack Anthony Has Reportedly Been Emily Osment's Boyfriend since 2021

Though Osment — who reportedly dated Meghan Trainor's now-husband, Daryl Sabara, in 2002 — has never spoken publicly about her relationship with Jack Anthony, he began appearing on her timeline in 2021. She only referred to him by his first name in her Instagram tributes, shrouding his identity in some mystery.

Still, certain outlets investigated and confirmed that he was indeed Jack Anthony. The couple frequently traveled the world together, visiting luxury destinations from Italy to Sweden. Osment hasn't tagged Anthony in her posts, but her tributes to him are always heartwarming.

She wished him a happy birthday in March 2022, writing, "well holy moly and happy birthday to my jack, love is real and you are mine." She did so again only days ago, gushing over her lover's traits, which included "kindness and silliness" and "a lust for life." Clearly, the lovebirds are still going strong.