Amabile, affectionately known to fans as Grocery Store Joe, made his Bachelor Nation debut during Becca Kufrin‘s season of The Bachelorette in 2018, but he was eliminated during the first week. The Chicago native later joined season 5 of Bachelor in Paradise, where he met Kendall Long.
Though the duo split before the season ended, they got back together during the September 2018 finale. “I’m happy with her,” Amabile told Us Weekly at the time. “I trust her. … We just like being together. It feels right.”
Less than two years later, however, the couple called it quits as they had difficulty deciding where to live. “We have decided mutually to go our separate ways,” they said in a January 2020 statement. “Joe has made the decision to move back to Chicago while Kendall will be remaining in her hometown of Los Angeles.”
When Amabile decided to give love another shot during season 7 of BiP, he immediately connected with Pitt, who originally competed on Matt James‘ season of The Bachelor in early 2021. The twosome seemed destined to finish the season as a couple, but things got rocky after Long arrived on the beach.
The California native ultimately decided to leave when she realized that Amabile and Pitt were endgame, but she returned a second time in the season finale, leading her fellow BiP contestants to wonder if she was there to sabotage the impending engagement.
“I don’t have any resentment — it was a little confusing,” the former grocer told Us exclusively after the October 2021 finale. “The timing, I would say, wasn’t the best. I was just really focused on Serena and getting to that moment. I had a ring in my back pocket. So it was more like, ‘OK, I get that you’re here, you know, I wish you the best, but it’s not the time. Now is not the time.’ But I hope she’s happy.”
Pitt, for her part, shared the same sentiment as her fiancé, telling Us at the time that she preferred to think about the future with her husband-to-be.
“I mean, I hope she’s happy,” the publicist explained. “I wish her the best. And, you know, we’re just happy to focus on our relationship now and kind of keep those special moments between us and keep them private and special in their own way.”
Keep scrolling for a complete timeline of Pitt and Amabile’s romance: