Emily Osment: From Young Sheldon Star to Personal Struggles.

In 1999, Haley Joel Osment delivered a mesmerizing Oscar-nominated performance as a young boy who can “see dead people” in M. Night Shyamalan’s chiller “The Sixth Sense.” It was a role that turned him into a household name across the globe practically overnight. However, in an interview with The Guardian several decades later, the former child star claimed that the glare of the spotlight was nothing compared to the one shone on his younger sister.

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Haley, who in 2024 made a rare must-see appearance to parody JD Vance’s tragic eyeliner, argued that having shot to fame as Miley Cyrus’ BFF Lilly on “Hannah Montana,” Emily Osment had “a way tougher path” to follow. “That show was squarely aimed towards creating a mania in that age group,” he said, referring to the Disney Channel phenomenon. “She had to deal with a lot more strange invasions of privacy, not being able to have a normal school life.”

Haley also acknowledged that his sibling had to grow up in the age of social media, something he resisted until his late 20s. Back in 2007, during the height of the “Hannah Montana” era, Emily told The New York Times that she was horrified to learn that hundreds of blog pages had been wrongly credited to her name and that she also didn’t appreciate being snapped by fans while traveling to and from the gym. “The Internet and anonymity really allow the crazies to flourish,” she explained.

In her 2020 Instagram Live show “Bright Minded, Miley Cyrus” glowingly introduced (via J-14) her former “Hannah Montana” co-star Emily Osment as “My BFF that shared the screen with me for the last 15 years.” On and off-screen she’s a badass best friend … Whether for Hannah or Miley, she’s always there for her.” But as the “Wrecking Ball” singer previously admitted herself, the pair weren’t always so close.

In her 2009 memoir “Miles to Go,” Cyrus admitted that she initially saw Osment, who played Lilly Truscott on the Disney Channel hit, as a threat: “There was competition between us — girls struggle with that, and we were no exception. I didn’t do much to fix it. I mean, I wanted to, but I had no idea how to go about fixing it. I never got along with girls as well as I did with guys.”

Cyrus also revealed that, in one of the many dark secrets the cast of “Hannah Montana” tried to hide, the pair would often get into fights whenever she did try to be more friendly. Luckily, their relationship changed in the third season of the teen phenomenon. “I think somewhere in the course of trying to keep the peace and act like friends, it sort of became true,” the Grammy winner wrote. “It felt natural.”

In 2011, Emily Osment received rave reviews for her performance in the ABC Family movie “Cyberbully.” The child star played Taylor Hillridge, a teenager who, after receiving a laptop for her 17th birthday, becomes the victim of constant online abuse. And it’s fair to say that the actor suffered for her art.

In an interview with TV Guide, Osment revealed she was regularly put through the wringer while shooting the cautionary tale in Montreal. “The hardest thing was being on set every day and having to get into the state of mind where I was crying. It was emotionally strenuous.”

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Plus, the tears didn’t stop flowing when the cameras stopped rolling, either. “I would just come home and I would cry,” Osment told We Love Soaps. “So, I would talk to my friends, especially my actor friends, and they’d call and I’d be like, ‘I just can’t talk to you right now,’ … And, they’re like, ‘Are you okay? This is not what you said you were going to be doing to this movie.'”

Having been subjected to a wave of online harassment playing the victim in “Cyberbully,” Emily Osment knows all about the pitfalls of the World Wide Web. And six years after laying her soul bare in the ABC Family movie, the actor revealed that she still finds it difficult to deal with the real-life keyboard warriors.

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“Cyber-bullying doesn’t have an age limit,” Osment tweeted in 2017 in a lengthy message inspired by a binge-watch of tough-tackling teen drama “13 Reasons Why.” “Even a [71]-year-old can be a bully. I still catch myself affected by what I read online in response to some of my more political or strident tweets.”

This wasn’t the first time that Osment had addressed the negative impact of social media. While promoting “Cyberbully,” the former child star revealed to We Love Soaps that she had an instant no-tolerance approach to any of her vocal detractors. “If I see something negative online, I truly will push ‘Delete.’ I truly will block the person whoever is sending it … But, you know the internet is the internet. It’s boundless and it’s scary and it can be very frightening and sometimes the best thing is to take yourself off of it.”

It seems as though every actor has a strong opinion on the necessity of intimacy coordinators right now, with Gwyneth Paltrow claiming that she’d feel stifled in the presence of one and Rachel Zegler arguing that they help to create a safe environment for all involved. While promoting the sitcom “Pretty Smart” in a 2021 interview with Decider, Emily Osment confirmed that she’s definitely in the ‘For’ camp.

“There’s this safe space feeling that I have been denied so many times in my career that I didn’t even realize I could ask for that,” the Californian explained about her support for the relatively new Hollywood job. “And not just because I’m an actor, this happens in every landscape of every job. Unfortunately, I can’t think of a single woman that hasn’t said ‘Yeah, I’ve felt uncomfortable in my place of work before.'”

In fact, Osment was integral to the appointment of a coordinator on the Netflix original. “They were like, ‘Oh sure yeah, we just didn’t think to do that,'” the actor revealed, referring to the producers’ response to her request. “Even if it wasn’t an intense moment, it’s always nice to have that person there. That was the first time as a number one I really put my foot down about something and wanted them to be hired. And we had the most wonderful woman named Rebecca [Johannsen] and that made a world of difference.”

In 2018, Emily Osment sat down to watch what would be the final season of “Young and Hungry,” the Freeform sitcom in which she starred as a young personal chef who falls in love with her tech millionaire client. Unfortunately, unlike the audience at home, she wasn’t laughing along.

“Special shout out to mental health,” Osment tweeted after the airing of one particular episode. “Your own sanity is so much more important than anything else.” The Californian then explained why she was struggling emotionally. “Weird seeing this season’s “Young and Hungry” from over a year ago when I was 20lbs heavier and deeply sad. Get yourself right. Get yourself first. It all falls in line.”

Osment has regularly taken to social media to address the issue of body positivity. During one of the many COVID-19 pandemic lockdowns, she posted a bikini-clad Instagram selfie captioned, “Nothing like getting in shape to see absolutely no one ever again.”

Emily Osment’s TV career has faced numerous setbacks over the years. In 2014, her action comedy “Cleaners” was canceled after two seasons. Her Netflix original “Pretty Smart” was axed after only one. And her CBS sitcom “25” never even made it past the pilot stage. Yet, the one that appears to have affected her most is the premature ending of “Young and Hungry.”

Osment spent five seasons playing Gabi Diamond, a young personal chef who enters into a relationship with Jonathan Sadowski’s nerdy tech genius, Josh Kaminski. The on-screen couple looked set to take things to the next level when the former proposed to the latter while also asking him to move from San Francisco to Seattle in one almighty cliffhanger. Unfortunately, its home network pulled the plug on the show before viewers got to find out the answer.

“It breaks my heart to tell you that in addition to Freeform TV not giving our “Young and Hungry” audience the ending our show deserved, they have ALSO decided to not go forward with a full-length film,” a devastated Osment tweeted (via Deadline). However, she did throw fans the tiniest of bones by referring to Sadowski as her “obvious future TV hubby,” suggesting that Gabi and Josh did get a happy ever after.

Before walking down the aisle for the first time, Emily Osment had several long-term relationships, none of which went the distance. And the majority were with guys no stranger to the showbiz world themselves.

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Osment’s first serious boyfriend was reported to be Tony Oller, a fellow Disney Channel graduate and formerly one-half of the soul-pop duo MKTO. Following their split, the Californian moved on to her future “Cleaners” co-star Nathan Keyes for a rumored 18 months before she started dating “Home Economics” actor Jimmy Tatro, whose real-life partner is now Zoey Deutsch. She also worked with the latter on several YouTube projects, including the short film “Fighting Couple” and the channel Drunk Questions, before the pair called it a day.

Perhaps sensing that mixing business and pleasure wasn’t working out for her, Osment then decided to try and date outside of the entertainment industry. In 2016, she entered into a relationship with Jim Gilbert, who worked at a charity named the Verdugo Hills Autism Project. It was an approach that appeared to pay off when the pair celebrated their fifth anniversary together. Soon after, however, they both decided to go their separate ways.

After several heartbreaks, Emily Osment looked to have found “the one” when she announced she was engaged to music producer and DJ Jack Anthony. “This love is so big and so uniquely ours and I know it can do anything,” the Californian gushed in a celebratory Instagram post (via People). Unfortunately, this big and unique love couldn’t withstand more than a few months of wedded bliss.

Indeed, putting a ring on it appeared to jinx things, as before the ink on the marriage certificate had even dried, Osment and Anthony headed for the divorce courts. In the papers filed by the former in March 2025, it was revealed that they’d actually separated just before Christmas, meaning their honeymoon phase lasted no longer than eight weeks.

Osment appeared to have taken the split in her stride, judging by the statement given to USA Today. “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,” the Californian said. “Ultimately, it didn’t work out.”

Emily Osment didn’t let the small matter of a worldwide pandemic stall her Hollywood career. During the lockdown era of COVID-19, the Californian still managed to film Netflix’s one-season wonder “Pretty Smart,” the TV movie “A Very Merry Bridesmaid,” and the third season of Netflix sitcom “The Kominsky Method.” But that doesn’t mean she wasn’t apprehensive about doing so.

Speaking to Us Weekly in 2021, Osment admitted (via Yahoo! News) that she was terrified about working throughout such a precarious time in history. “It was scary to be in a position where you don’t really know if you’re safe or not. And you have no choice but to pick up your mask and work.”

The Disney Channel graduate, however, did have some emotional support while reprising her role as Theresa in “The Kominsky Method” thanks to her Academy Award-nominated older sibling, Haley Joel Osment. “Knowing where he’d been — you know, he’s my brother — it was comforting to have him there,” she added.

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Many celebrities found themselves on the front pages in 2025 due to the raging wildfires that consumed much of Los Angeles. Although Emily Osment wasn’t directly affected, she did have to support the family members who were.

The “Spy Kids 2: The Island of Lost Dreams” saw both her older brother, Haley Joel Osment, and her parents, Michael and Theresa Osment, lose their homes in the disaster. “It’s been an extremely difficult month,” she wrote in an Instagram update. “Community is everything and I know I’m heavily leaning on mine right now, and that’s okay! So much love for my beautiful, aching city.”

Osment, whose shaky start to the year was compounded by her divorce from her husband of just five months (Jack Anthony), went on to ask her followers to help out in any way they could. “Please find some time to donate and show up and be there for those who are struggling right now,” she added. “We’re all doing our best and that really is enough.”