The duo was first photographed together while shopping at a flea market in Pasadena, CA on January 12, 2020. At the time, sources told TMZ, “Josie and Logan recently started dating, with things turning romantic after years of running in the same friend circles in Los Angeles. Hollywood can be pretty small.” The insider also revealed that “things are off to a great start.”
But on February 21, 2020, reports hit the web that the couple had split. The social media star later confirmed the break up to Life & Style, telling them that he’s “single as a Pringle” and that he and Josie were “not that compatible.” He also admitted that her past relationship with Brody Jenner contributed to their downfall.
“I was in the midst of all that s–t. I was like, ‘I’m going to dip pretty quickly,’” he said.
As for what he looks for in a girl, the vlogger explained, “I have qualities on my phone. It’s so unrealistic, though. My expectations are so f–king high. They’re so high. I demand excellence and I expect the person that I’m with to demand excellence of me. If I don’t deliver, then they should be on their way. Likewise, like I want an opinionated girl. I want an intelligent girl and I live in L.A., so intelligence is hard to come by.”
He also explained during an appearance on the “No Jumper” podcast, “I was like, ‘I don’t know if I can give more right now, this is the best I got’ … I wasn’t, in this particular scenario, ready to give myself in that way. She left my house that night … we haven’t texted or spoken since. Both of us ghosted each other, it’s a mutual ghost. It was a very mutual, like okay, it’s clear this was fun, but we’re not compatible. At the end of the day, we’re not.”
Then on May 4, 2020, when the influencer uploaded a new YouTube video featuring his ex, some fans quickly started to speculate that they were back together. He then confirmed to Entertainment Tonight that they were indeed going strong again! He also told the outlet that they were quarantined together, and opened up about how they met.
“It was a crossing of L.A. circles,” he explained. “She’s over here and I’m over there and we crossed circles one night … It’s f–king serious. It’s pretty serious. Yeah.”
On June 15, 2020, the social media star revealed he had gotten her a pretty epic gift — a horse! Naturally, he documented the whole thing for a YouTube video, and boy, was it adorable.