Jason Tartick Gushes Over Bond With Bachelor Nation’s Kelley Flanagan

Jason Tartick has nothing but positive things to say about fellow Bachelor Nation alum Kelley Flanagan.

When cohost David Arduin noted that Tartick, 36, and Flanagan, 33, had “good chemistry” while recording the Monday, March 31, episode of the “Trading Secrets” podcast together, Tartick replied, “She’s great. She’s just awesome. She’s easy to be around. She’s funny, she’s kind, she’s sweet, she’s smart.”

During the Monday episode, Flanagan discussed a work project that she’s keeping under wraps — which led Tartick to ask about a “potential date maybe this summer.”

“Were you referring to a date of when we’ll hear about her project, or did you just slyly say maybe we will have a potential date this summer? I need to know because the people need to know, too,” Arduin asked, to which Tartick set the record straight. “Let me just clear it up. I’m referring to the project, but you know, who knows, David,” Tartick said.

Arduin noted that “sometimes the best relationships come from people who start as friends,” but added that he’s “not going to push it.” Tartick replied, “You would be a fan of it. You would push this, I feel like.”

Tartick explained that it’s possible he and Flanagan could be in the same location this summer due to his Rewired Talent organization. (Tartick is a Managing Partner and Founder of the company.)

“I will say this, we are talking about getting a Rewired Talent management house in the Hamptons this summer. Little tease. She was like, ‘I want in. I want to be part of it. I’m down chip in, whatever it is,’” Tartick claimed. “So yeah, we might be in the Hamptons this summer.”

Tartick noted that he and Flanagan “keep in touch,” adding, “I would say Kelley and I talk on the phone at least once a week, catching up. Especially in the last month or so.”

Related: Peter Weber and Kelley Flanagan’s Relationship Timeline

Peter Weber and Kelley Flanagan’s relationship has been unconventional from the start. During the January 2020 premiere of season 24 of The Bachelor, fans learned that the attorney ran into the pilot at a hotel in Malibu in August 2019. “Kelley met Peter prior to the taping of the show,” Chris Harrison revealed in January […]

While Flanagan did not end Peter Weber’s season of The Bachelor engaged, the pair rekindled their romance offscreen. After several months together, Flanagan and Weber announced their split on New Year’s Eve in December 2020 before reconnecting in early 2021. They broke things off again in 2021 before getting back together. Flanagan and Weber called it quits for good in 2023.

When asked by Tartick whether there’s anything she would have “done differently” from when she went on the show until now, Flanagan replied, “The way Peter and I started dating was one of the messiest things that you could get together with someone. So that caused a lot of stress — maybe not as dramatic, maybe not as messy, maybe a little bit calmer.”

Flanagan moved on with Ari Raptis, but confirmed in a November 2024 episode of the “Chicks in the Office” podcast that she is single. While reflecting on her dating life, Flanagan claimed men and women from Bachelor Nation have different experiences post-show.

“I think the guys in the franchise are different from the girls because the fan base is girls. For you guys, I think it’s a little bit harder. Like, I’ve been out when I used to date Peter and I was always with the boys. The fan base reacts differently to the guys than they really do to the girls,” Flanagan said.

Flanagan, who said she “barely ever talked about the show” in her last relationship, continued, “You guys date the people that are usually watching the show, like the fanbase. A lot of the guys who, I would say, we probably date, maybe haven’t even really watched the show or aren’t like crazy fans, don’t know so much about it and aren’t really involved in the drama. They’re more so out. It’s different for us, because the guys we are usually dating aren’t intertwined to some degree.”

Tartick noted that dating is “just hard.” (Tartick was previously engaged to former Bachelorette Kaitlyn Bristowe before pursuing a relationship with influencer Kat Stickler. Tartick and Stickler called it quits in 2024.)

“2025 is a whole different f***ing ball game out there,” he said. “I find that dating is, like, a full-time job.”