When did Logan Paul’s and Olivia O’Brien date? Ex-girlfriend shares wrestler’s past comments on kids

Logan Paul has gained fame thanks to his controversial beginnings on YouTube and his present life as a WWE wrestler, boxer, and podcaster. In addition to his professional life, his romantic life has also gained a lot of attention over the years.

One of his most discussed flings has been with American singer-songwriter Olivia O’Brien. Even though they never officially addressed the rumors, their connection goes as far back as 2013 and includes music collaborations and several public appearances together.

In an interesting turn, Olivia O’Brien weighed in on their history by giving her take on Logan’s approach to fatherhood. Recently, underneath a TikTok post that showcased Logan’s new show with his brother Jake Paul, American Olivia reminisced about a personal moment they shared. Under the TikTok post, she commented, saying:

"He once told me he wanted to have a kid because he loves himself so much, he thought he could only love someone else fully if it was ‘half of him’ like it was a science experiment,"

Speculations about Logan Paul and Olivia O’Brien dating surfaced in late 2019. Though they never publicly said they were in a relationship, both Paul and O’Brien confirmed that they had a romantic and sexual relationship.

O’Brien later said in an interview with Nick Villa that they hadn’t been exclusive but had been in an on-and-off relationship for a while.

Logan Paul is currently engaged to Danish model Nina Agdal. The pair's first child, daughter Esme Agdal Paul, was born on September 29, 2024. They got engaged in July 2023 while on a trip to Lake Como, Italy.

More about Logan Paul's history with Olivia O’Brien and his new show

O’Brien was initially hesitant to reveal the song, Josslyn’s inspiration. She rejected that it referred to any one person, instead describing it as a reflection of emotional pain brought by unnamed men.

But eventually, she admitted that the song was about Logan Paul. In a subsequent interview, she suggested that there’d been more than one song about him.

O’Brien’s performance at Coachella 2022 led to more gossip, as Logan Paul invaded the stage for O’Brien’s performance for Josslyn. Waving a sign that said “It wasn’t worth it,” a reference to the lyrics, Paul’s surprise appearance ignited fans to speculate that the couple were back together.

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Logan Paul’s new Max reality series, Paul American, is said to focus on the Paul family, fame, and scandals. The series, according to Variety, combines scripted and behind-the-scenes moments to showcase their quest to stay relevant in a media-centric world.

The series shows Logan struggling to navigate his WWE career with his new role as a father and even covers Jake Paul's story as he was getting ready to face Mike Tyson.

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