Olivia O’Brien Dating History and Past Boyfriends

Olivia O’Brien boyfriends

When there is a rumor, there’s suspicion. The notion is an appropriate one for Olivia O’Brien’s romantic stories.

After being romantically linked with some of Hollywood and YouTube’s famous stars, Olivia keeps her secret close to her side.

Despite her perseverance in keeping everything under the rug, some fans might argue that she has already dropped her credibility regarding her information about one tale we will discover later.

Olivia O'Brien is single

With that in mind, her fans also wondered whether the Californian-born singer currently has someone special near her. One source claimed that Olivia indeed has a boyfriend in her life.

Olivia uttered that she has someone special whom she regarded as “a real gentleman.” Olivia even said that she and the mysterious Mr. X went on an 11-day date after her European tour.

Who might Mr. X be? There are two things for sure. Many suitors are waiting for her, and Olivia can pick anyone she wants. Remember, she is still young yet already a famous singer. Another thing to consider is that the singer seemed happy with her new relationship. As we will learn later, Olivia met and dated some quite indecent men.

So, let’s take this moment and rewind the time to when Olivia O’Brien was still trying to comprehend the difference between love and lust.

Olivia O’Brien and Logan Paul: Friends or Lovers?

Olivia O’Brien and Logan Paul
Olivia O’Brien and Logan Paul

Let’s start with the main course, shall we? Olivia O’Brien and Paul Logan have been in constant observation from both fanbases. The attitude and the comments made by the pair certainly made everyone suspicious, especially when talking about their relationship.

Logan and Olivia began to make a small ripple in Hollywood when Olivia released her song “Josslyn” in 2020. It was just a simple song about two lovers separated after the “boy” never tried to be honest with his feelings for her. However, many fans then commented that the song poked at Logan’s attitude toward Olivia.

The suspicion began to swirl even harder when Olivia appeared on Logan’s podcast “Impaulsive.” The clumsiness of both Paul and Olivia made it clear to their fans that something was happening between them.

Also Read: Kian Lawley and Girlfriend Ayla Woodruff: An Instagram Love Story

Seemingly trying to answer their fans’ questions, Paul and Olivia appeared together in London in 2021. The pair went on a casual lunch date before going off to an undisclosed location together by car. The moment coincided just after Olivia told the press that she had Paul’s name in many of her songs.

“I made several songs for him. I’ve lost count of just how many pieces. It all started when I felt heartbroken; I approached him and said I wanted him in my bed tonight. I had and even today have romantic feelings for him.” Well, Olivia, we all know who “him” is, so let’s be more honest here.

Recently, Logan attended Olivia’s performance at the 2022 Coachella. With a huge banner, Logan wrote, “It wasn’t worth it” on the stage. Later, Olivia told the media that she and Logan had their best time as friends.

“We feel happy around each other. I’m lucky to have a good friendship status with your so-called YouTube star.”

Is it the endgame for Logan Paul and Olivia O’Brien? Maybe, for now.

Was Pete Davidson indeed dating Olivia O’Brien?

Olivia O’Brien and Pete Davidson
Olivia O’Brien and Pete Davidson

Logan Paul is not the only guy with a spectacular romantic tale with Olivia O’Brien. During her time with Logan, Olivia opened her heart to another man named Pete Davidson, an American actor and comedian.

The rumors occurred in 2021 when a Twitter account named DeuxMoi told Twitter viewers that romantic feelings were there to see between the “Love Myself” singer and the “King of Staten Island” actor.

Even though the pair initially seemed to deny or remain silent, in 2022, Olivia unexpectedly confirmed the rumor was true. Came to a podcast as a guest, Olivia O’Brien cannot hide her shock after hearing that most fans already knew there was a romantic relationship between her and Pete Davidson.

“How did you know this? How? It’s mad! How could you know about this?”

After being caught off-guard, Olivia revealed that she once dated Pete before it ended in 2020. The singer told the media that Pete broke her heart with a simple message, “I can’t see you anymore. I have a new girl.”

Also Read: Jason Mantzoukas Ex-Girlfriend Praised Him As the Best Thing, But It Wasn’t Enough to Make Her Agreed to Be His Wife

Olivia remarked on her relationship with Pete that Pete was a “Nice guy, adorable, and the most important thing, he was funny.”

Unfortunately, Pete Davidson’s spokesperson told the media that the rumors about Olivia and Pete were false. However, the declaration didn’t deny that the two were good friends.

Todd Smith and Olivia O’Brien: Was he too kind for the singer?

Olivia O’Brien and Todd Smith
Olivia O’Brien and Todd Smith

If there is a sentence that completely describes Todd Smith’s relationship with Olivia O’Brien is that he was too warm for Olivia’s bleakest heart. Olivia appeared on a podcast where she said she would not make a song about Todd Smith.

Olivia told the podcasters that she gave a “good guy” a chance once, but it ended since Olivia never felt it was suitable for her.

“I have these tattoos on my left arm. Inside the tattoos, if you can decode them, are the names of guys that had utterly wreaked havoc inside my life. But that’s just me. I love guys that had no intention of dating me but destroyed me anyway. The same guys that utterly treated me as junk,” said Olivia.

Olivia O'Brien tattoos on her left arm
Olivia O’Brien tattoos (Photo: Instagram)

“But, I gave and tried the love he gave me—the love from a guy that enamored my existence. He was adorable, warm, and seemed too good for me. I felt terrible for him, and after it, I said goodbye. Since I had no feelings left for him, I didn’t write songs about him. I want to respect him as he did to me back then.”

So, with that, that is the end tale of Todd’s romantic journey with Olivia O’Brien.

Was love developed between Grayson Dolan and Olivia O’Brien?

Olivia O’Brien’s romantic story with Logan Paul was quite a scene to read. However, it wasn’t the first time that Olivia got involved romantically with a YouTube star.

Back in the day, some sources claimed that Olivia once dated a YouTube star named Grayson Dolan; however, since there was no confirmation of the rumors, many thought of this as simply a prank or hoax by the fans.

DJ Gnash: More than just a producer for Olivia O’Brien?

Olivia O’Brien and DJ Gnash singing
Olivia O’Brien and DJ Gnash (i hate u, i love u in the BBC Radio 1 Live Lounge)

We finally reached the final list of men with a special place inside Olivia O’Brien’s heart. This time, we take you to the first man who knew the potential of Olivia O’Brien. He was DJ Gnash, and maybe he might seem unfamiliar to you; Olivia remembered him well.  

It was not a stretch to say that DJ Gnash was the one who gave Olivia a chance to enter the music industry. It all started when Olivia covered Gnash’s song “Disposable” and uploaded it to the internet. The producer took notice of it, then personally contacted Olivia before offering her a career in the music industry.

Everything went perfectly well for the two, and before we knew it, Gnash and Olivia released a song called “i hate you, i love you” in 2016. However, many commented that Gnash was just a producer for Olivia O’Brien. A source claimed that the pair had a couple of outings in Los Angeles before Olivia released her original debut song.

But, it remains unconfirmed, and even though we are grateful for Gnash’s approach to nurturing Olivia’s talent, we would like him to address this.

About The Author (864 Posts Published)

Rosa has a passion for movies and TV shows. She is creating content and handling editorial work for Creeto, focusing on Celebrity news.

Notify of
Inline Feedbacks
View all comments