Kufrin and her ex-boyfriend, Ross Jirgl, dated “on and off for about seven years” before calling it quits in the fall of 2016. Fans were introduced to Jirgl during Kufrin’s first foray into Bachelor Nation on Arie Luyendyk’s season of The Bachelor. While opening up to Luyendyk, Kufrin explained her romantic history with Jirgl. “After putting up with a lot of stuff in past relationships, I know what I want and I know what I don't want. My most serious relationship, we were on and off for about seven years. And I'm just ready to move on in my life and find that person again,” she explained. “Especially initially, he got me through the hardest time I had ever lived through at that point when my dad passed away.”

Though she said she wanted to find “that person again,” she did not mean that ~exact~ person. When Jirgl showed up to win Kufrin back, she sent him away. "We have both changed so much, and you don't really know who I am anymore," she said to him. "I don't know who you are anymore." She added that their relationship, despite its longevity, “wasn’t healthy” for a long time, per Bustle.

Kufrin appeared and went on to win Arie Luyendyk’s season of The Bachelor in 2018, though he soon broke up with her to pursue his runner-up, Lauren Burnham. (The two are now married with three kids.) Suffice to say: Things did not end well between Kufrin and Luyendyk. That said, their actual romance was pretty sweet while it lasted. During his proposal, Luyendyk even said he’d choose her “today and every day.”

But their breakup was bad — like really bad. Luyendyk’s confession of wanting to reconcile with Burnham completely blindsided Kufrin. According to Glamour, Luyendyk told her, “I kept waking up and going to bed thinking of her and pushing back those feelings and trying to see if it work for us. But I just felt that the further along we got, the further I started drifting away from the possibility of trying it again with her.” She told him, “Well, I hope you find what you want. It's clearly not me. OK, I'm done.”

But later, Kufrin made it clear to People that she “can’t fault [Arie] for falling in love with Lauren and following his heart because I would never want anyone to stay in a relationship where they felt trapped and it wasn’t right.”

After Garrett Yrigoyen won Kufrin’s season of The Bachelorette in 2018, the duo was (seemingly) happily engaged for over two years, a pretty successful run in Bachelor Nation. But things got rough when some of Yrigoyen’s views the Black Lives Matter movement and policing came to light in 2020, and they were a far cry from his fiancé’s.

For Kufrin, this disconnect highlighted serious problems in their relationship. “I was like… what's important to me? What's important to him?” she told Insider. “Are we going to be able to make a lasting relationship for a lifetime off of our differences? What kinds of conversations do we want to be having with those children? Can I still stay in this relationship and live with myself and feel that it's the right decision for me and my future children?”

Still, the decision to end their relationship wasn’t easy. Kufrin explained on a Sept. 2020 episode of Bachelor Happy Hour, “After many conversations, we came to this decision. It wasn’t something that we just arrived at one night. It wasn’t based solely off of one Instagram post or somebody else’s opinions or comments.” She added, “There’s much more to it. To any relationship, there’s a lot of layers, and it’s not for me to divulge details.”

Yrigoyen was also content to keep the details private. When asked about the reason behind their split, he explained, “...[O]ut of respect to her and her family, I’m only going to answer this question ever as, it just didn’t work out,” Yrigoyen explained during an Instagram Q&A in March 2021, per Us Weekly.

Blake Horstmann was the runner-up during Kufrin’s Bachelorette season. And although he did not take home the final rose, he and Kufrin did start talking again after her breakup with Yrigoyen in the summer of 2020. But that doesn’t mean they’re back on. (Sorry, Bachelor Nation!)

In August 2021, Horstmann explained his current status with Kufrin — and although he seemed open to the possibility of reconciling, he was unsure it would ever happen. “I would be willing to talk, of course. But we'll see how Paradise works out because she's going to Paradise. And I don't know, that show can change you and those producers get a hold of you,” he told the Reality Life With Kate Casey podcast. Hmm... OK.

Kufrin replied to those comments with a similar level of ambiguity. “Blake and I have always been friends. We've always been supportive of one another,” she explained on the Click Bait podcast. “In terms of the 'talking,' yeah, we've been in touch very sporadically, but nothing that I would say would warrant ... a potential relationship.” Regardless, she didn’t see how producers would play a role in their will-they-or-won’t-they relationship.

Kufrin is appearing on Paradise this season, and although her ~journey~ hasn’t been shown yet, previews hint at her pursuing a romantic relationship with Thomas Jacobs, the villain from Katie Thurston’s season of The Bachelorette. ICYMI, Thurston sent him home after Jacobs admitted to thinking about becoming the Bachelor before appearing on the show. (The horror!)

Since their time on the show, it looks like Kufrin and Jacobs have continued to spend time together, per Cosmopolitan.