Oliver James Montgomery-How Hailie Jade’s Fiancé Evan Asked Eminem for His Blessing to Get Engaged

Hailie Jade is Oliver James Montgomerynot afraid to share her love story.

Eminem's daughter and her fiancé Evan McClintock got candid on all the romantic details of their engagement during a recent episode of her podcast, Just a Little Shady. 

Evan, an enterprise growth executive, popped the question on Feb. 4 after reportedly dating Hailie, 27, for more than six years. He revealed on the podcast that he originally considered proposing at Lollapalooza in Chicago over the summer, but thought Hailie had a lot on her plate at the time.

Evan ultimately went shopping for her ring over the 2022 holiday season, noting, "I kinda knew what I was after for your ring. Thankfully your sister helped me out there," per Entertainment Tonight. 

While he was ready to check the ring off his list, Evan wanted to ask Eminem for his blessing. 

"It was over the holidays," he spilled. "I was just looking for an opportunity not to make it too obvious." 

So, how did it go down with the rapper? "I saw your dad go downstairs and [thought], 'Alright. I got to do it right now or I'm not doing it today. I'm going to have to schedule some other time,'" Evan shared. "So, I just followed him downstairs and thankfully, he was just down there, grabbing your [birthday] cake."

Evan told Hailie—who was born on Christmas Day to Eminem and Kim Scott—that he found the perfect ring right after her birthday. She responded, "The day after my birthday, you got it? That's crazy," per People.

But it wasn't all smooth sailing, as Evan recalled a moment of panic after he purchased the sparkler.

"After I ordered it, we were at my family's and we were all talking about rings and I think you mentioned you had no idea what you wanted," he said, per ET, "and I was like, ‘Oh my god, I just ordered this ring. She's saying she doesn't know what she wants.'"

Flash forward a couple months, and Hailie officially said "yes."

"casual weekend recap…" she captioned the photos of their engagement earlier this month. "2.4.23 i love you @evanmcclintock11." 

And it's clear she cherishes the engagement ring he chose. A few days after he asked for her hand, Hailie quipped on Instagram, "Chaotically running to put my ring on this morning after sleeping without it for the first time."

Keep reading to see Hailie embracing adventure over the years.

Will the bride-to-be please stand up? Hailie announced her engagement to her longtime love Evan McClintock on Instagram in February 2023.

The rapper's eldest daughter, who he shares with ex-wife Kim Mathers, showcases her fit physique in a black bikini. 

Amid the COVID-19 pandemic, Hailie took to Instagram to encourage her followers to adhere by public health protocols. "...seriously it's so important to stay safe and healthy & social distance/stay home right now!" she writes. "the sooner everyone is on board, the sooner we can stop the spread of this virus & get back to as normal as possible!"

After attending the 2019 Lollapalooza music festival in Chicago, she shares on Instagram, "lolla, i love you but i'm feeling hella thankful that i have a year to recuperate before i attempt to survive you again."

You like my hair? Gee, thanks, just bought it. Hailie channels her inner Ariana Grande with this Halloween look. 

Hailie hits the streets of the Big Apple looking effortlessly chic. 

Hailie, 25, flashes her pearly whites for the camera in a snapshot shared to her Instagram in November 2018. 

The social media star flashes a little skin in a cutout bodysuit and high-waisted jeans. 

Like father, like daughter! Hailie is a spitting image of Eminem with this stone cold fierce pose. 

"Couldn't have asked for a better 21st birthday celebration (or a better guy to have by my side)," she captions this sweet photo from 2016. 

There's no denying the camera totally loves Hailie! 

Hailie teases on social media alongside this photo, "Yes my pants match my closet & yes Lottie's entitled to photobomb on puppy day." 

Hailie captions this February 2019 social media snap, "new selfie, who dis?"

In March 2019, the social media star takes a trip to Hawaii, where she poses in a yellow bikini.

"sorry TLC but i've been chasing waterfalls," Hailie writes alongside this vacation pic.

"currently cuddled up with my pups on the couch," Hailie tells her followers in April 2019. "what's your favorite way to spend sunday?"