The event not only marked the red carpet debut for the rapper and social media personality, but it also marked their first date together — something Yung Gravy and Easterling have been looking forward to since the beginning of July.
In addition to Rae, Easterling shares sons Enzo and Lucas with estranged husband Monty Lopez. The two originally split when Rae was young, remarried in 2017, and recently separated again.
From how they met to their red carpet debut at the VMAs, here's everything to know about Yung Gravy and Easterling's relationship.
July 14, 2022: Yung Gravy and Sheri Easterling spark romance rumors
On July 14, Yung Gravy uploaded a video to his TikTok that featured a compilation of Easterling's social media pages highlighting the "single mom" text written in each bio. The rapper concluded the video by overlaying himself over her Instagram profile as he stared at the camera with a smile.
That same day, Easterling uploaded a TikTok of herself using a generator that predicted her next date. While the random shuffler generated a "picnic in the park with her dog," she edited the outcome by posting Yung Gravy's name over it.
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Soon after, the rapper "stitched" a response to her upload. The first part of his TikTok was a repost of her video, while the second part was him exclaiming, "Oh, it's on site baby!" He captioned it, "Name a time and place," adding "#gravyrae."
The flirty, back-and-forth TikToks continued throughout the month of July along with the pair writing a handful of playful comments on each other's posts.
Aug. 3, 2022: Yung Gravy talks about his attraction to Sheri Easterling
Jamie McCarthy/Getty Yung Gravy and Sheri Nicole Easterling
When Yung Gravy appeared on the BFFs podcast on Aug. 3, Dave Portnoy asked him about his interest in dating older women.
The rapper, deemed "the MILF guy," candidly spoke about his attraction to Rae's mom, noting that it was Easterling who made the first move.
"She basically showed some love and DMed me at one point," Yung Gravy said of the mother of three. "So I started showing some love back and now we're just being cute." He added, "We're making videos back and forth and sending little wholesome DMs."
While neither of them had met in person at the time, the rapper disclosed that he planned on taking Easterling out on a date.
Aug. 14, 2022: Yung Gravy reacts to Sheri Easterling's relationship with her estranged husband Monty Lopez
While Rae has yet to publicly react to her mom's romance with Yung Gravy, the rapper mentioned the TikTok star during an interview with Zach Sang Show as he talked about Easterling's complicated relationship with her estranged husband.
"I just feel bad," Yung Gravy said. "I feel bad for his daughter. I feel bad for his ex-wife Sheri." He revealed, "[Sheri] hit me up and was like, 'Don't get involved,' so I'm steering clear."
Aug. 28, 2022: Yung Gravy and Sheri Easterling make their red carpet debut
Johnny Nunez/Getty Sheri Nicole Easterling and Yung Gravy
At the end of August, Yung Gravy and Easterling had their first date at the 2022 MTV VMAs. Easterling accompanied the rapper at the award show, where the two made their red carpet debut and shared a kiss for the cameras.
Aug. 28, 2022: Yung Gravy reveals how he and Sheri Easterling first met
During the VMAs preshow, Yung Gravy opened up about how he connected with Easterling online before meeting in person, telling MTV that they hit it off "right away."
"I'm from the furthest north it gets, she's from the furthest south it gets," Yung Gravy said of Easterling. "I'm into MILFs and she's kind of the queen of MILFs, so I figured it was just a perfect match."
Aug. 28, 2022: Monty Lopez reacts to Yung Gravy and Sheri Easterling's relationship
Immediately following Yung Gravy and Easterling's red carpet debut at the 2022 VMAs, Easterling's ex Lopez posted his thoughts on his Instagram Story.
"Unbothered!" he wrote over a shirtless photo of himself. "Thank you @yungravy for taking the leftovers! I would rather spend time with my daughter and 2 grandkids that Sheri Nicole made me abandon as a child in order to be with her!"
He concluded, "Never let a woman make you choose between her and or your blood child."
The following day, Lopez seemingly shaded Easterling and Yung Gravy's relationship again as he posted a video alongside the text, "When you're dating 20 year olds and then…"
The video featured a cartoon person — with Lopez's superimposed head — running through the streets while being chased by a cop car as he mouthed the lyrics, "It's cool when they do it, it's a problem when I do it. F— 'em."
Aug. 29, 2022: Yung Gravy defends Sheri Easterling on Twitter
Following the couple's romantic red carpet debut at the 2022 MTV VMAs, the "Betty" rapper came to the defense of Addison Rae's mom when a tweet said that Easterling was "causing quite the internet stir" due to their PDA-packed date night.
Yung Gravy retweeted the post — featuring a clip of him kissing Easterling on the red carpet — and wrote, "She's newly single and living her life. leave her alone lol."
she’s newly single and living her life. leave her alone lol https://t.co/ib4PrQIJ2H
— Gravy Timberlake (@yunggravy) August 29, 2022
October 7, 2022: Sheri Easterling and Yung Gravy call it quits
Easterling and Yung Gravy's relationship ended after roughly two months of dating.
"It was very short-lived and they wanted to get people talking," a source close to Easterling told E! News. "Sheri definitely was interested in him and loved the attention but they both knew it wasn't going to be anything serious."
November 14, 2022: Yung Gravy says distance played a part in his breakup with Sheri Easterling
During an interview with Amazon Music, Yung Gravy addressed his former relationship with Easterling.
"It was a good day. It was a beautiful day," he said, referring to the day he and Easterling made their red carpet debut at the VMAs. To which the host asked: "You didn't want to continue the day?"
"She lives in Louisianna," Gravy responded.