There's no doubt that Miley Cryus is the biggest star to have come out of Disney Channel's Hannah Montana. She did play the titular character, after all. But Miley has also been the type of star who has gravitated toward the limelight. Therefore, we know pretty much everything there is to know about her love life. Less is known about her former co-star, Emily Osment, and what really goes on with her romantic life mostly because Emily keeps a much lower profile. So much so that some fans still wonder what happened to Emily Osment. Her die-hard fans, however, know that she's been on a few notable projects since Hannah Montana, namely The Kominsky Method and Young & Hungry, and currently stars on Netflix's Pretty Smart.
While these die-hard fans know where to watch Emily, they still aren't sure who she is dating. And a look at her Instagram account doesn't exactly reveal all the information. It does, however, show that Emily absolutely does have a boyfriend at the time of this writing. Here's what we know about him and their relationship...
Emily Osment's Past Boyfriends And General Dating History
Emily Osment has a lot of guy friends. While she clearly has a lot of friends in general, there's always a guy around her for fans to confuse for her boyfriend. So, naturally, Emily has been said to have been involved with a lot more men than she likely has. However, there are a few she absolutely has dated.
According to Distractify, one of Emily's longest relationships was a 6-year-stint with Jim Gilbert. The two apparently met through a mutual friend and not through the business. In recent years, Emily has done a pretty good job at not dating actors or anyone remotely connected to Hollywood. While little is known about Jim, we do know that he was a therapist.
During the course of their relationship, Emily's Instagram followers would occasionally get a photo of Jim, albeit often obscured. Emily has done a very good job keeping her romance with Jim private. However, there have been times when Emily has posted a very clear photo of her and Jim, including one of them kissing while in swimwear on the beach.
While Jim was clearly a very big part of Emily's life, the pair called it quits sometime early in 2021. Since then, all of Jim's photos have been removed from Emily's Instagram account. Either things didn't end well or Emily really wanted to move on after investing so much time into the relationship.
Prior to Jim Gilbert, Emily was reportedly involved with actor Jim Tatro. The paparazzi have snapped the two together at numerous functions, holding hands, and even kissing. Emily and Jim Tatro dated for about two years but were very public. Yet, once again, Emily maintained some privacy on her social media accounts.
Emily was also rumored to be linked to her Spy Kids 2 co-star, Daryl Sabara in 2002 (although this is unlikely as well). The same was said for her and her Hannah Montana co-star, Mitchell Musso. Then there's Nathan Keyes who has been photographed with Emily in various tocuhy-feely positions. Something very well could have gone on between them but Emily calls him her "forever friend" to this day.
We do know that Emily absolutely dated actor Tony Oller for a couple of months while the two were just teenagers. The copious photos of the two engaging in PDA proved that.
Emily Osment's Current Boyfriend In 2021 Is Jack Anthony
While many 'updated' publications claim that Emily is still with Jim Gilbert, they clearly haven't been paying close attention. Not only has Emily removed all of Jim's photos from Instagram, but she has also started posting a ton with her new boyfriend. While she had done a great job hiding her new non-famous boyfriend's name, his face is included in quite a few images as is his Instagram handle... Turns out, Emily is now dating a guy named Jack Anthony.
Back in August 2021, Emily and her new man explored various coastal cities in Italy. While he was featured in a few of the photos from the trip, Emily only included shots of him from behind or from afar. Still, fans could see that Emily has a type... Tall, blonde, skinny, and not a pretty, actor boy. As part of the same trip, Emily and Jack went to Sweeden. In the images, the two could be seen cuddling up together.
While their trip to Sweeden was filled with hangouts with friends, their trip to Italy was far more romantic. Again, Emily has done a lot to hide Jack at the back of her photo collages, but a quick swipe through reveals that these two are totally serious about one another and must have begun dating sometime shortly after she and Jim broke up in early 2021.
Even though fans are waiting for Emily to become a little bolder in revealing details about her new man, it's clear by all of the shots of them enjoying Phish concerts, extravagant vacations, and days in Disneyland that the two are in a serious relationship.