[4] O'Brien initially gained the attention of Gnash after posting a cover of one of his songs on SoundCloud, after beginning to create music at the age of 13.

[5] Gnash reached out to O'Brien, expressing interest in her material, and asked for her to send him any original songs that she had.

[8] Thereafter, O'Brien signed with Island Records and released her debut solo single, "Trust Issues", in August 2016, which premiered through Complex magazine.

[15] O'Brien made her television debut in July 2016 with Gnash performing "I Hate U, I Love U" on Late Night with Seth Meyers.

[18] In March 2017, O'Brien was nominated for an iHeartRadio Music Award for Best Solo Breakout, but lost to Zayn Malik.

[25] O'Brien released the lead single, "I Don't Exist", in September, followed by "Care Less More" in November, both with accompanying music videos.

[34] A track from the tape called "Josslyn" gained traction on streaming services and radio airplay when users on TikTok began doing dance challenges to the song.

[37] A remix with rapper 24kGoldn was released on May 22,[38] whilst the original song was serviced to top 40 radio formats on June 2.

[47] However, Olivia decided to take a step back on the release of the second half of the album for now, saying she "[doesn't] want to worry about making a project right now", and that she's "just putting out songs at this point" on the Zach Sang Show.

In March 2023, O'Brien announced via TikTok that she left Island Records due to a variety of differences.

[49] In April, she released "Born With a Broken Heart," her first single as an independent artist, followed by "I Should've Fucked Your Brother" in July.