While some Bachelor and Bachelorette couples make it down the aisle, others can barely wait for their finale to air to call it quits.

Peter Weber, for his part, may go down as the only Bachelor to have two breakups in such a short period of time. The season 24 lead originally proposed to Hannah Ann Sluss in November 2019, but ended their engagement in January 2020 because he had unresolved feelings for Madison Prewett.

“I should’ve really picked up on the first red flag you gave me — that you wanted to reach out to Hannah Brown to find closure with her,” Hannah Ann told Peter during their first confrontation after their breakup at the live After the Final Rose in March 2020. “So really, looking back on it, our engagement involved three women: Me, you still being in love with Madison, and you needing closure with Hannah Brown. Word of advice, if you want to be with a woman, you need to become a real man!”

Following Peter and Hannah Ann’s split, then-host Chris Harrison went to Alabama to tell Madison it was over. While Peter and Madison made plans to take their relationship one day at a time during the After the Final Rose taping, they were over two days later.

“Madi and I have mutually decided to not pursue our relationship any further,” the pilot wrote on Instagram at the time. “Believe me this was not easy for either of us to be OK with, but after a lot of honest conversations, we have agreed that this is what makes most sense for the two of us. The love and respect I have for Madi will continue to endure.”

She added at the time: “As Peter and I have decided to go our separate ways, I am confident that we will both move in the direction of our purpose and never forget that God has a plan in all things,” she wrote. “I will always love and respect him. I am convinced our paths were meant to cross and we are both better because they did. @pilot_pete you are an amazing guy and I’m thankful for you. I will always be your biggest fan. And to the amazing women I met this season, I will love you for life.”

Peter and Madi may win for the shortest relationship, but they certainly aren’t alone. Scroll through to some of the shortest — and most memorable — Bachelor Nation romances: