Matt, 29, wore a brown and black plaid suit with oversized sunglasses while his date rocked a a black long-sleeve bodysuit featuring a plunging neckline and sheer floor-length panels.
Matt and Rachael, 24, took pictures together at the awards show, and Matt also posted a photo of the couple posing with basketball player Paige Bueckers on his Instagram Story, according toUs Weekly.
Several weeks ago, The Bachelor couple enjoyed a romantic vacation to Aspen, Colorado.
An eyewitness at the Little Nell luxury resort, where the couple stayed in June, told Us that Matt and Rachael "weren't hiding" their affection for one another.
"[Their] Aspen getaway was very romantic," the source shared.
"Both were bright-eyed, easygoing and in a very joyous mood. It's very obvious to onlookers that they are definitely headed in the direction of an engagement... They were very close and acted as if they had been dating for years."
Matt gave Rachael his final rose on The Bachelor's Season 25 finale, which filmed in late 2020, but the couple split in February when racially-ignorant and racially-insensitive photos from Rachael's past resurfaced online, including a 2018 image of Rachael attending an antebellum-themed "Old South" party at her Georgia college with sorority sisters.
Matt explained on The Bachelor: After the Final Rose in March that he wanted to give Rachael some time to educate herself on racism in society and gain awareness. Matt apparently needed to know that Rachael could support him and truly understand his perspective as a Black man in America.
But according to Reality Steve spoiler blogger Steve Carbone, Matt could only stand his breakup from Rachael for about a month because he allegedly began texting and FaceTiming her every day following their ATFR appearance, saying he still loved her and wanted her back.
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Matt and Rachael apparently reunited on April 4 in New York City to give their relationship another shot, and they proceeded to hang out in Los Angeles and Miami before becoming an official couple again.
"There were rough patches in our relationship," Matt acknowledged during the May 25 episode of The Pomp Podcast, likely alluding to the fact he had been accused of trying to hook up with an old Miami-based flame named Grace shortly before flying Rachael to New York to see him in early April.
Matt explained there was a point in time when he "wasn't really honoring" the commitment he had made to Rachael to work on their relationship" but a "come-to-Jesus meeting" with the brunette beauty got the couple's romance back on the right track.
"We are back together now," Matt confirmed at the time.
"[Rachael] was like, 'If you're going to make this work, then let's do it. But, if you're not going to make it work, then I'm going to let you do your own thing.' That's really all I needed," Matt recalled.
Matt added, "The best thing about Rachael is her heart. She's the most kind, caring, and understanding person I've ever met... Everything we've been through, everything she's been through, she's stuck right by my side. She's continued to have a positive attitude."
E! News reported in early June that Matt and Rachael had begun discussing the possibility of Rachael relocating from Georgia to New York City, where Matt currently resides, and moving in together.
"Matt and Rachael are in a really good place right now and are getting serious. They are inseparable and talk all day, every day," a source close to Matt told the website last month.
"They have been making many plans to see each other so not a huge chunk of time passes before their next visit... [Rachael] has always loved the city, so it would work out well."
The source added that Matt "is truly in love" with Rachael and they "have a special bond" and "really turned a leaf in their relationship."