Olivia O'Brien's Boyfriends: Her Known & Rumored Romances

Olivia O'Brien has established a solid fan base following some of her hit songs that tell her real-life story. Now fans are curious about the singer-songwriter's love life and who Olivia O'Brien's boyfriend is.

O'Brien is a successful singer-songwriter. She received global attention following her hit song "I Hate U, I Love U," in which she collaborated with Gnash. Through her talent and creativity, the 23-year-old has won the hearts of many, and fans can't stop jamming to her songs.

When the talented singer wrote a song about one of her boyfriends, she raised fans' curiosity, with many interested in her dating life and some wanting to know whether Olivia O'Brien has a boyfriend.

Olivia O'Brien Has Never Been in Love

O'Brien hasn't talked about her love life lately, so whether she is in a relationship with someone is unknown. However, she once revealed that she had never been in love. "I don't think I've ever actually been in love with anyone, like mutual love. I really don't," she said in an interview.

In July 2022, during an interview with BFFs' podcast, O'Brien was shocked when hosts Dave Portnoy, Josh Richards, and Bri Chickenfry asked her if she was once in a relationship with comedian and actor Pete Davidson.

The questions caught her off-guard as she thought no one knew if she and Davidson had a romantic relationship. The singer then explained she and Davidson talked for about five months and would only hang out in person a few times because they lived far away.

However, during an interview, the California native dismissed the rumors, noting that she and Paul were good friends.

O'Brien said that even though she hung out with the comedian, it was far from an exclusive situation, which came to an end via text.

"He texted me and was like, 'I'm seeing someone else," she said. However, she explained she and Davidson were cordial and even described him as a nice guy. "He's hot, and he's really funny, and he's really sweet," she said.

However, Davidson dismissed O'Brien's claim that they briefly dated in 2020. He told Page Six the information was false, noting that the two were friends and only hung out a few times.

Olivia O'Brien's Last Known Relationship Ended In a Breakup

In 2021, O'Brien confirmed in an interview that she had met someone and briefly discussed the relationship.

She met her unidentified man, who works in finance, when she was in a great place and not thinking about being in a relationship. They started to hang out, and she liked his vibe. After 11 days together, she still had butterflies.

In April 2022, she revealed she had gone through a breakup; however, it's unclear if the split was with the guy she had mentioned in the previous interview.

O'Brien reportedly also once dated singer, DJ, and influencer, Todd Smith. The two dated for a while, but O'Brien broke up with him, noting that Smith was a nice guy, and admitted she didn't treat him right.

The Song "Josslyn" Is Based on Olivia O'Brien's Personal Experience

O'Brien once revealed that some of her songs showcase her vulnerability. She stated in an interview the story behind her song, "Jossyln," and said it was about a guy she was talking to, and then she discovered he was cheating on her.

Olivia O'Brien Denied Rumors of Dating Logan Paul

O'Brien was once rumored to be in a relationship with media personality Logan Paul. However, during an interview, the California native dismissed the rumors, noting that she and Paul were good friends. Also, O'Brien explained the whole story behind bringing Paul on stage at Coachella, noting that it was his idea to get on stage.