In February 2017, O'Brien released "Empty" as the lead single from her debut extended play.
In March 2017, O'Brien was nominated for an iHeartRadio Music Award for Best Solo Breakout, but lost to Zayn Malik.
She released the next single from the EP in July, "RIP", with accompanying music video.
The third single, "No Love", followed in November along with her debut extended play, It's Not That Deep.
O'Brien featured in the acoustic version of Jack & Jack's single "Beg", released in January 2018.
In June 2018, a remix of "RIP" was released with the collaboration of G-Eazy and Drew Love.

In August 2018, "UDK" was released as the first promotional single from O'Brien's debut studio album.
O'Brien released the lead single, "I Don't Exist", in September, followed by "Care Less More" in November, both with accompanying music videos.
The third single, "Love Myself", was released on February 1, 2019.
In March, O'Brien announced that her debut studio album, Was It Even Real?,
was scheduled for release on April 26, 2019.
She then released "Just Friends" as the second promotional single, and "Just a Boy", as the final single before the release of the album.
In May 2019, O'Brien collaborated with the Norwegian group Seeb on "Fade Out".
The single was accompanied by a music video.
In February 2017, O'Brien released "Empty" as the lead single from her debut extended play. In March 2017, O'Brien was nominated for an iHeartRadio Music Award for Best Solo Breakout, but lost to Zayn Malik. She released the next single from the EP in July, "RIP", with accompanying music video. The third single, "No Love", followed in November along with her debut extended play, It's Not That Deep. O'Brien featured in the acoustic version of Jack & Jack's single "Beg", released in January 2018. In June 2018, a remix of "RIP" was released with the collaboration of G-Eazy and Drew Love.
In August 2018, "UDK" was released as the first promotional single from O'Brien's debut studio album. O'Brien released the lead single, "I Don't Exist", in September, followed by "Care Less More" in November, both with accompanying music videos. The third single, "Love Myself", was released on February 1, 2019. In March, O'Brien announced that her debut studio album, Was It Even Real?, was scheduled for release on April 26, 2019. She then released "Just Friends" as the second promotional single, and "Just a Boy", as the final single before the release of the album. In May 2019, O'Brien collaborated with the Norwegian group Seeb on "Fade Out". The single was accompanied by a music video.
Olivia O'Brien