Prior to her relationship with Jim Gilbert, Emily was in a relationship with the ever-so-funny Jimmy Tatro. The pair were together from Oct. 2013 to March 2015.
Distractify reports, "They apparently met through a mutual friend, which makes sense because Jimmy, although a well-known YouTuber at the time, was just starting to break into television and movies."
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The couple was private about their relationship, feeling there was no reason for them to flaunt their love for others to witness and potentially judge. Before Emily's relationship with Jimmy, she dated Nathan Keyes for a little over a year. Based on this Instagram post from 2019, it seems the two are still friends today!
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According to WhosDatedWho, Emily Osment dated MTKO frontman Tony Oller from 2009 to 2010. Not much is known about their relationship, but the two were both Disney stars at the time, so that clears up how they met.
