April 14, 2026 pillow talk
Josh Dated Taylor Frankie Paul’s Sister Before ‘The Bachelorette’ — And There’s More
Talk about a backstory!
As Bachelor Nation fans know, the most recent season of “The Bachelorette” is currently on pause.
While viewers wait to see what happens next, the men from Season 22 have been appearing on the “Bachelor Happy Hour” podcast to exclusively discuss how they’re feeling and share more of their stories.
This week, Josh stopped by to spill some lore about his connection to Taylor Frankie Paul before “The Bachelorette,” including dating her younger sister Aspen when they were in school.
“We go way back. I actually grew up with Taylor’s family. I went to school with them, played sports with some of her cousins, we’ve been in contact for… oh, man it’s been almost, not 20 years, but like 15-plus [years]?” he said. “Her mom has driven me to some of their family parties… I think we ended up going to different high schools because I think she and her family ended up moving closer to when she was finishing high school and we’ve got a little bit of an age gap. But I was really good friends with her younger sister and her cousins, so we definitely swim in the same circles.”
Josh went on, clearing the air about his relationship with Taylor’s sister.
“There’s rumors that float around and I’ll put those to ease. I’ve never been engaged to or married her younger sister Aspen. But we did [date]. That was never anywhere close to the extent,” he said. “We were boyfriend and girlfriend, me and her younger sister, for I think two whole days… We were sixth graders, I think we were 12 years old, little kids. We passed a little note to each other: ‘Will you be my girlfriend? Will you be my boyfriend? Yes or no?’
“And that’s the history made itself, so we just stayed best friends forever and that was pretty much the extent of it. It wasn’t anything drastic, but really good friends. Always support each other over the years through her growth on — like Taylor’s growth on TikTok.”
Josh went on, “I mean during COVID, we talked a lot during that time because she was jumping in the mix of TikTok and I helped a lot of people kind of catch some steam there. And so she was asking for tips and tricks and we connected. We made some fun little fake pregnancy videos on there to just catch the public’s eye.”
Josh then clarified that it was Taylor, not Aspen, who he was making TikTok videos with.
“Me and Taylor,” he confirmed. “We were duetting each other’s TikToks, we had been talking a lot. So prior to the Mansion, tons of Story swipes, tons of Instagram conversations about her kids, her family and how she’s doing, and her spiritual growth that she’s had. I feel like she’s — girl’s gone through a lot! I mean to each of us, we all do, life’s not easy. And so we were able to connect on a lot of different things that were subtle and simple over the years. I’m definitely someone of integrity and I knew that for a while there, she was married to a really great guy. And so there was no intent or anything like that, and that application of pursuance. But when the door was opened and she was open to it, that’s where opportunity — I had the opportunity to strike and here we are.”
Hear the rest of Josh’s interview, including which one of Taylor’s family members he reached out to after getting chosen for her season, in the full episode below!