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How One 17-Year-Old Went from Ivy League Hopeful to Ruling the Radio

“I Hate U, I Love U” is only the *start* of Olivia O’Brien’s success.

How One 17-Year-Old Went from Ivy League Hopeful to Ruling the Radio
Alec Kugler

I discovered Olivia O’Brien the same way I discover most new music nowadays: via Instagram Stories. Her R&B-based tunes—which include the radio hit “I Hate U, I Love U”—tend to make the perfect soundtrack for those crappy, eff-everything kind of days. Or the ones where you’re feeling reflective. Or when you’re actually pretty happy, but want something you can sing along to. The bottom line? Olivia O’Brien is really, really good. And her songs are catchy enough that I immediately Googled her after listening.

The most surprising thing I later learned about this singer? She’s only 17, and therefore just getting started in this biz. Read on for the facts you need to know about young-yet-soulful Olivia, like how fame was a surprise and why she’s choosing to be completely honest rather than faking it on social media.


How her hobby became her career:

“I never really thought of it like ‘Oh I’m a singer [and] songwriter.’ I thought of it more as ‘This is something I do.’ When I was little, I thought that everyone wrote songs. Then, when I started showing people, they were like, ‘Oh, this is good!’ I was like, ‘Okay, maybe I have some kind of talent.’ Then I started posting, and things kind of escalated from there.”

The moment when she knew she had to pursue music:

“Probably when ‘I Hate U, I Love U’ was starting to get radio play. I didn’t think anything would happen. I was going through photos of myself the other day, and I found a photo of myself—my friends had made a cake for me when I hit 100,000 streams on SoundCloud. I thought that was the biggest thing ever! Little did I know like what would happen. [laughs] It was all a surprise.”

About her song “RIP”:

“I really like ‘RIP.’ It’s definitely more reflective of me and who I am right now. [With] ‘I Hate U, I Love U,’ I didn’t think anyone was ever going to hear it, so I just kind of wrote it for myself when I was feeling emotional. I was a freshman in high school. I haven’t thought about the boy I wrote that song about in years. I’m excited to kind of have my own thing [that’s] reflective of my personality, my individual style, and that’s a better representation of myself.


If she ever gets nervous about being so honest:

“Everyone has the same feelings, people just don’t always talk about it. If I talk about the way I’m feeling, chances are there’s other people feeling it too and people are going to relate to it, no matter how out-there it is.”

On breaking the rules, and singing about drinking and doing drugs:

“I think I took things too seriously when I was younger. I had a 4.5 GPA in high school, I was planning on going to an Ivy League college. I just thought that everything had to be exactly right in my life for me to be successful. I tried to fit in when I was in high school, and when I realized that I didn’t have to, that was kind of where I found my happiness. I was like, ‘Oh hey, I can actually be an individual person and do my own thing, and I don’t have to give a fuck about what other people think.’ That’s when I started to break the rules. And obviously I’m not an alcoholic or drug addict at any means, but, everything in moderation.

“My whole thing is, I don’t want to have to have some kind of scandal where people see me at a club or something. I don’t want to have that drama, so I might as well be honest with people and tell them what I do so I don’t have to lie and get caught up in some kind of fake stuff. When I go out or am at a party, I’ll see people that will literally tweet ‘I hate alcohol and drugs,’ and then I’ll see them doing serious drugs. Are you okay? Why are you saying that on the Internet but are doing this? I just don’t want to be like that.”


Whether she enjoys switching up her look and keeping up with beauty trends:

“I just like to change things because I get bored. So I was like, ‘I’m going to dye my hair pink! No, I’m going to dye it brown! No, I’m going to dye it blonde! No, I’m going to dye it purple!’ And I cut my hair myself. I was literally like, ‘Fuck this, I’m cutting my hair off.’ I think it’s more of me trying to mix it up, rather than trying to keep up with beauty trends. Not that I’m like some kind of huge trendsetter, but I like to start them and do my own thing and see if people will follow.”

If she envisions herself being in this industry forever:

“Yeah! I dropped out of high school, so hopefully I don’t have to do anything else. I’m pretty confident that this is going to work out for me because I love it, I care about it, and I feel like I have what it takes. I used to really doubt myself, but [discovering] what I’m capable of has inspired me to work harder and really turn this into something that I’m proud of.”


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