At the heart of the issue were racially-charged photos from her past and what he saw as her lack of understanding of what it was for him to be a Black man in America. He told her he wanted her to take the time to do the work alone, even as he admitted he cared about her.
It was a controversial decision at the time, with some finding it insensitive of him to not be by her side while she did the work as her remorse felt genuine. At the same time, Matt had his supporters, too, who felt it wasn't his job to educate her as to how systemic racism continues to exist in this country.
As controversial as their breakup was, the pair drew even more attention when they started being spotted out and about together a few months later. Headlines dominated the media with pictures of them walking, talking and even -- gasp! -- holding hands!
Finally, they put all the speculation (not that it wasn't obvious) about their relationship status to rest on Saturday by hitting the ESPYS red carpet together, looking very happy and cozy together in the process.
While there, they spoke about some of the additional challenges that they faced coming of the first-ever season of "The Bachelor" with a Black lead, that then found itself embroiled in multiple racial controversies (Chris Harrison parted ways with the franchise after what many saw as him defending Rachael over her pictures at an Antebellum South party).
"I will say that, you know, of course it was difficult in the moment, but just being able to step back and work on our relationship to assess," Rachael told People at the ESPYS. "Taking a moment away from the spotlight's been really good for us. It's been a lot better."
With the additional focus on the franchise due to Matt's status as the first Black Bachelor, and the additional focus on racial issues, theirs was the most high-profile finale for the show in many years. It's easy to see why in the middle of that massive spotlight wasn't the best place to navigate such a difficult and nuanced situation.
Once the media turned its attention away from them, they were able to reconnect and regroup. The connection they felt for one another was palpable, both during the show and even during that finale.
It was clear that Matt was fighting his own emotions in turning Rachael away, but he felt this incredible societal pressure on him in that moment, too. What was the right thing to do? What did he want to do? What should the first Black Bachelor do?
Once away from all of that pressure, they were able to slow down and think about what it is that they wanted to do. And that was to continue to explore their feelings, even as Rachael was continuing to do the work to be anti-racist in her own right.
Since they appear to have figured out how to make a go of it despite that enormous pressure, Matt was asked if he had any tips for romance, with him joking that probably no one should listen to his advice.
Instead, he says he's looking at those relationships that have stood the test of time, like Rachael's parents. "I think that I look to people who have been where I'm trying to get to," he explained. "Relationships that are prospering are what I kind of fix my eyes on and hope to emulate."
Matt confirmed that he and Rachael were giving things another shot during an appearance on the "Pomp" podcast in May. He said it happened in part because Rachael gave him an ultimatum, causing him to realize he wasn't putting in the work he'd promised.
"It was honestly a commitment that we made to each other that we were going to work on the relationship," he said then. "There came a point in time where it was evident that my working on the relationship looked different than Rachael’s because I wasn’t really honoring that commitment that I made to working on the relationship."
"She was like, ‘If you’re going to make this work, let’s do it. But, if you’re not going to make it work, I’m going to let you do your own thing,'" Matt explained. "That’s really all I needed,” he explained. “It was an ultimatum that I needed. It’s been great.”