For almost a decade, Keeping Up With the Kardashians has entertained millions of fans with their sometimes outrageous antics and silly situations, but the usually upbeat reality show was anything but during last night’s episode—season 9, episode 7—as Rob, Khloé and Scott Disick all dealt with some seriously heavy issues.

While most episodes leave us with our abs sore from all the laughing, this episode, titled “The Courage to Change” left us with pits in our stomachs.

It isn’t often that a reality show has us reaching for the tissues… but that was definitely the case last night. Check out the five saddest moments.