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Olivia O’Brien Will Never Give A Cheater A Second Chance

On her new EP, she explores unrequited love and the lessons she’s learned.

by Marilyn La Jeunesse

“I have this feeling that I’m gonna quit music this year and live on a ranch somewhere,” 24-year-old singer-songwriter Olivia O’Brien wrote on Threads in July 2023. Fast-forward one year later, and while O’Brien did temporarily trade the Los Angeles cityscape for the more serene views of Nashville, Tennessee, she hasn’t quit music… yet.

On June 21, O’Brien released her latest project, a five-song EP titled Love and Limerence she wrote while living in Nashville, inspired by her experiences with dating and heartbreak. “I’m a person that gets stuck in limerence a lot,” she tells Elite Daily. “[The EP] is about unrequited love, obsession, and the unattainable side of love. I think that’s something a lot of people can relate to, and it’s certainly been my experience in dating.”

O’Brien has long channeled her own love lessons into her songs, famously writing the 2020 track "Josslyn" about her ex Logan Paul. While she admits she’s never had a relationship lasting longer than six months, she’s not in a rush to find The One. “I always say no dating until marriage,” she jokes. “I am enjoying being single, probably more than most people.” Still, she has one hard-set rule when it comes to new relationships: no more cheaters.

Here, the pop crooner opens up about going through messy breakups, dating as a bisexual woman, and analyzing her birth chart.

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Elite Daily: Your lead single on the EP, “glimpse of me,” is about self-growth and moving on from a relationship that doesn’t serve you. Can you tell me a little about the inspiration behind the song?

Olivia O’Brien: I wrote a letter to a person that I had a relationship with on and off for a really long time. I wasn't ever going to send it to them; I just wrote out everything I’ve ever wanted to say, including, ‘you only saw a glimpse of me.’ I felt like he never saw who I actually was and only saw what I possibly could have been through his eyes, and he pigeonholed me as this timid, fragile girl and never got past that. I felt so unseen and unheard, so that song is my love letter to myself.

ED: The track “blip” talks about how you can love someone with your whole heart and mean nothing at all to them. Was this written about someone in particular?

OO: Actually, no. It's just something I’ve experienced time and time again with my relationships. I always felt like I cared about people so much more than they cared about me, and I was just someone they could throw away, whereas they were everything to me. Pretty much every relationship I've ever had, that's been the case.

ED: What do you do to heal after going through a breakup?

OO: I don't. I never get over anything ever.

ED: That begs the question: What is your zodiac sign?

OO: I'm a Sagittarius, which doesn't make any sense in that regard. I'm not a relationship person — you would think I would be based off of my music, but all of my songs are about situationships. That's the Sagittarius in me.

I also have a Cancer moon, so I’ll get really sad and emo, and there’s a deep desire within me to be loved. My Venus sign, which represents the way you think about love and relationships, is in Libra, so I idealize and romanticize relationships a lot.

Point blank, period. Cheaters are the worst.

ED: We have to talk about your 2022 Coachella set, where Logan Paul walked out with a sign that said “it wasn’t worth it.” What was it like to have an ex admit he messed up so publicly?

OO: He didn't admit anything. We just thought it would be funny, and we were still friends at the time. I thought it was a hilarious little prank. I had just broken up with another person, and I wanted to piss him off a little bit. So I thought, “Oh, I'll just call Logan and have him come out.” I knew my ex was going to be there, and I just thought it was the funniest thing.

ED: Do you have any advice for someone who’s been cheated on?

OO: It's never your fault, ever. Literally, Beyoncé got cheated on. A lot of the time, someone can't handle being with someone who makes them feel insecure, so that's why a lot of the coolest, greatest people will get cheated on because their partner can't handle it. You have to just move on and realize that that person sucks. Point blank, period. Cheaters are the worst.

ED: Would you ever give a cheater a second chance?

OO: No. F*ck no. Not ever.

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ED: What’s the worst date you’ve ever been on?

OO: I moved my age range up on Raya because I was hating everyone and hadn’t been on a good date in a long time. I wanted to see what the older men were doing.

I saw this guy, and it seemed like we had so much in common. He rock-climbed at my gym and loved Greek mythology. He was 36, a writer, and he seemed perfect. I went on a date with him, and he was the most arrogant *sshole I've ever met in my life.

I was telling him to his face, “You're arrogant. You're an *sshole, you're a prick. You think you know everything.” But he loved it because he was so egotistical that he thought I was flirting with him the whole time. He asked if I wanted to get ice cream afterward, and I had to run and escape him. I wish I could have recorded the whole thing because I have never met a more horrific man in my life.

ED: Speaking of red flags… is it a red or green flag if they’re still friends with their ex?

OO: Depends on how long ago they dated. Especially in the queer women community, it’s the most common thing in the world. Everyone is still friends with their exes.

If a guy is friends with his female ex and it hasn't been more than five years since they broke up, then I think it's weird. Also, how close are they? If they're close, no. If they're cordial, green flag. You don't want them to hate each other. Hate is the closest thing to love; that means there's still something going on there.

ED: What are your thoughts on making the first move on someone?

OO: I'm so bad at it. That's been the hardest thing for me with dating women. Men are constantly on the prowl, and it’s easier because I can be like, “OK, fine.” I have a huge fear of rejection, and I also just have zero rizz. If I actually see a future with someone or think they're genuinely cool, I have the hardest time acting normal.

ED: You’ve obviously dated in the celeb and influencer world, but would you ever date a fan?

OO: The problem with having a presence online is that people develop a parasocial relationship with you. Even people who aren't necessarily fans have preconceived notions about me, and that has been a huge problem in dating.

Even if you’ve seen every interview and done all your research, it’s not an accurate representation of me. So I’m going to have to say no, I can’t do it, because I don’t want to disappoint someone. Ideally, I would like to date a person who has no idea who I am, who lives in the forest and doesn't have social media. That's the dream.

This interview has been condensed and edited for clarity.