The Truth About Emily Osment's Dating History

Almost every millennial and Gen Z kid knows who Emily Osment is. Even before her iconic role as Lilly Truscott in the hit Disney series Hannah Montana, Osment had been working in Hollywood since she was a small child. She played the lead, Gabi Diamond, in the series Young & Hungry up until 2018. After that, she starred in hit shows like The Kominsky Method and Almost Family, and she voiced various characters in the animated show Family Guy. From her pop music to her acting career, it seems as though Osment keeps dishing out new surprises. 

One of the biggest surprises is what's happened in her dating life. While many people secretly wished that she and former Hannah Montana co-star Mitchel Musso would've dated in real life, she's dated a lot of other dreamboats. From actors and YouTubers to normal nice guys, Emily Osment has had an interesting dating history. Yet somehow, she keeps her dating life as private as she can.

Emily Osment has been in a relationship since 2016

In late 2009, Tony Oller and Emily Osment were spotted together multiple times, looking snuggly. Not much is known about their relationship, although they were together for quite a few months (via WhosDatedWho). Osment's next public relationship wasn't until the following year, with fellow actor Nathan Keyes. Since Osment keeps her relationship details more private than most, not too much is known. But what we do know is that they dated a little over 18 months and took many photos together, per WhosDatedWho. An Instagram post from 2019 shows that they're still good friends today!

Osment's next beau was Jimmy Tatro, who dated the Disney alum for a few years. In an interview (via YouTube), Tatro said the pair met through a mutual friend. They worked together on a few short films, one of which was "Fighting Couple" (via YouTube), as well as a series on Tatro's YouTube channel called "Drunk Questions." It's unknown when they broke up.

Emily Osment decided to stop dating celebrities and started dating current boyfriend, Jim Gilbert. She started dropping hints on her Instagram in the summer of 2016 and quickly revealed him less than a year later. According to J14, who first disclosed their relationship, they found out that he's a "normal" guy who worked at Verdugo Hills Autism Project. Whether or not he still works there is unknown. Nearly five years later and the pair still seem like they're on Cloud 9, via her Instagram.