By the simple nature of how reality stars come into our lives, it’s easy for us to get swept up in their stories and feel especially connected to them. That can make it extra hard (for fans) when their beloved celebrities go through breakups. It’s even worse when those couples are from The Bachelor, The Bachelorette, or Bachelor in Paradise, because all we want, from the second we meet them, is for those stars to find love.

Fans were crushed when Kaitlyn Bristowe and Shawn Booth ended their three-year engagement recently, and in their honor, we’re revisiting some of the most painful Bachelor Nation splits. Scroll through the gallery to see them all!