The 38-year-old radio host got very candid and emotional in a pre-taped package, where he opened up about his teenage hardships and the loss of his mom, and explained why 1998, the year he became the first person in his family to graduate high school, meant so much to him.
Speaking with ET's Katie Krause on the carpet after the show, Bones explained why he wanted to share his emotional story with America.
"I hope that people are touched by [my story]. I think that's why I tell my story so that people don't feel so alone," Bones shared. "I think I felt very alone for a lot of my life but once I was able to share my story more and more and people wouldn't say, 'Hey I felt sorry for you,' but, 'I get it and I understand you,' it kind of encouraged me to tell it more. I just don't want people to feel alone."
During the tearful package -- which played right before he and partner Sharna Burgess took the stage for their routine -- a picture-in-picture feature (which is new to this season) gave viewers a look at the host as he watched his own segment while getting very choked up.
"I didn't think it was going to affect me like it did," he admitted. "I mean, it's a story that I've written in a book and I talk about on the radio but to watch it back and then do something uncomfortable like dance which I don't know how to do yet, [was tough]."
During the show, Bones opened up about how much graduating meant to him, considering his mom's struggle with drug and alcohol addiction and a father who disappeared. According to Bones, his mother was inspired by his graduating to earn her GED, but sadly died from her addictions when she was in her 40s.
For their dance on Monday, Burgess choreographed a contemporary routine set to "A Million Dreams" from The Greatest Showman soundtrack, and the emotional performance served as a tribute to his mom, and his own perseverance as a kid.
"It's always a lot of pressure when you take someone's truth and you try to put it into dance and Bobby has such an incredible story and I wanted to capture it in the right way and with something that he connected to," Burgess explained to ET.
"One of the things Bobby told me was that when he was a kid, he found solace in books and reading and trying to build his knowledge and find a way out of his situation," she continued. "And so I wanted to build this space where this kid was dreaming and reading and when he told me his story, instantly 'A Million Dreams' came to my head."
Following their powerful performance, Bones was brought to tears as he sat by the edge of the bed that served as a central prop in their routine, and had a hard time finding his words as he spoke to the judges.
The pair earned 23 out of 30 for their efforts on Monday -- their highest score of the season thus far -- and a round of praise and support from the judges and his fellow stars.
The emotional display from Bones was a far cry from the wild exuberance he exhibited following his routines during the first two weeks. In fact, Bones' celebratory nature may have hurt the couple after their New York Week dance, when he ended the number by performing the viral dance move the Floss, which confused the judges.
ET caught up with Bones and Burgess after that night, and the pro admitted she was a little mad at the radio host for not finishing the dance as planned, but didn't want him to change who he was. Check out the video below to hear more from the couple.