The move came as a surprise to viewers, as Matt chose to end things with Michelle before going on his last date with his other potential pick, Rachael Kirkconnell.
The breakup came after Michelle, who was one of five women to enter the season late, met Matt's mom, Patty, earlier in the episode. The introduction went well, with Michelle telling Patty that Matt was "the one" for her, and Patty gushing over Michelle's "sweet heart."
"Michelle continues to set the bar high," Matt said at the time. "... I'm extremely excited about where we're at in our relationship. You never know how something's going to go, you just cross your fingers and pray. Today couldn't have gone any better."
After tense conversations with both his mom and Chris Harrison, though, Matt questioned if he was ready to get engaged at all. Matt and Michelle's date repelling down a building initially went well, but Matt admitted he was struggling dealing with the "gravity" of the situation.
During their nighttime date, Michelle once again expressed her love for Matt and gifted athletic jerseys that read "Mr. and Mrs. James."
"I'm sitting here and I am in love with you and I cannot imagine having anyone else as my teammate at this point. It's you. It's you that I want," she said. "It's hard to picture leaving here without you."
At that moment, Matt told the camera that he has "doubt" about his relationship with Michelle.
"I feel terrible. I didn't know this is how it's going to feel," he said. "I don't want to do anything that's going to break her heart, but when you care about someone you just gotta let them know."
He then confessed as much to Michelle, telling her that it's "the first time I've felt anything outside of wanting to be with you forever."
"I've been pushing through that feeling today and trying to get there because of how I feel about you," he said.
Michelle asked for "clarity" on the situation, asking whether or not she should fight for him and their relationship.
"I don't think I can get there with you," he responded.
"It's hard to feel like you have this connection with somebody and they flip a switch and it's gone," she cried.
"I don't want you to think it was a flip of a switch," he insisted as Michelle continued to sob.
Michelle walked Matt to the door, where he apologized before leaving. After departing Michelle's room, Matt told the cameras that it wasn't "a good feeling" to breakup with Michelle, especially since he "really cares" about her.
The Bachelor even questioned if it was the right decision, before tearfully admitting to Chris Harrison that he doesn't know if he can continue with the show.
"It's been a long time since I cried," he said through tears, adding that he loved Michelle, "but wasn't in love with her."
Before Matt and Rachael appeared on After the Final Rose, Michelle opened up to host Emmanuel Acho about her emotional split.
According to Michelle, she was ready to get engaged to Matt and felt he was truly the one for her.
"After I saw how my family accepted him, he was able to, like, slide right in, that's the moment that I did think he was the one," she shared. "By that time, I had kind of seen the interactions that were happening, and that was kind of the icing on the cake for me."
Which made Matt's decision to send her home all the more painful, and Michelle admitted it was a conversation that she didn't see coming.
"It really just felt like one of those moments where all of your blood, everything, leaves your body, and seeing it for the first time, watching it back... It's a lot," she shared.
She also said that she wasn't given an opportunity to find closure, or to speak with Matt after their split.
"Afterwards, I wasn't okay, and I needed to say my piece, because I didn't get the chance to," she shared. "So I asked if I could talk to Matt for two minutes, and not to change his route, to not get in the way of the relationship that he was pursuing that was still there. It was just for me to say my piece."
"But he refused to have that conversation with me," she added. "I think I deserved the two minutes to get my closure and move on."
When Matt joined Michelle on stage, she once again spoke about her disappointment over not getting that final conversation with him.
"The moment you left, I completely crumbled. I had to walk away without closure, and I had to fill in the gaps of what our relationship really was. I wasn't OK. I wasn't OK at all," Michelle told Matt. "Producers were in my room, seeing how bad I was hurting, and I asked you for a conversation. It was not a conversation where I was trying to change your trajectory or trying to change your mind or fight for you. It was a conversation so that I could have my inner peace when I left Pennsylvania. And you said no."
"I'm sorry that you were going through that. There's no justification for why I didn't have that conversation, and if I would have known that this is how you were feeling in that moment, then I would have fought to have that conversation," Matt responded. "... If I could do it over again, I would have had that conversation with you, knowing how you feel, and all I can say now is I'm sorry."
The conversation ended on a friendly note, with Michelle telling Matt that "it does help hearing that what you felt for me was real, and... we were on the same page, somewhat, up until that point."
"You have taught me a lot about relationships and what I'm looking for and what I'm not looking for at times, but you will always hold a piece of my heart. I hope you find your happiness," she said before quipping, "I hope you move on with kissing with your eyes closed. I hope you come up with more phrases than just, 'Thanks for sharing.'"
Follow along with ET's coverage of the Bachelor finale and the After the Final Rose special here.