All About Kylie Jenner's Best Friend, Influencer Stassie Karanikolaou (2024)

YouTuber Anastasia “Stassie” Karanikolaou has been in the Kardashian circle for more than a decade.

She met her now-BFF Kylie Jenner in middle school, and the two have been inseparable since.

"She's definitely my oldest friend," Jenner said of Karanikolaou on the season 3 finale of The Kardashians. "We grew up together, we've been through so much together. She's like a sister."

Despite being an internet personality in her own right — Karanikolaou has close to 11 million followers on Instagram, where she was long known by her previous username, "stassiebaby" — a great deal about Karanikolaou's upbringing remains largely unknown. The story of how she came to meet Jenner is another widely unknown fact. (Spoiler alert: it was not at a fan event, despite many theories.)

Between her YouTube channel, which has more than 770,000 subscribers, and a tell-all interview on Alex Cooper’s Call Her Daddy released last year, Karanikolaou has been open about what her life is like now that's she's cemented herself as a public figure. But, when it comes to her past, the details have emerged slowly.

Karanikolaou told Cooper that she tends to avoid interviews because she gets “so nervous” talking to people, which has played a part in how private she’s kept her early life.

From first meeting Jenner in a bookstore in middle school to now being one of the Kardashian clan’s closest confidants, Karanikolaou has had quite a journey in the public eye.

So, who really is Stassiebaby? Here’s everything to know about the model and influencer who is one of Kylie Jenner’s best friends.

She's from Los Angeles, and she and her sister were homeschooled

Despite living a lavish lifestyle now, Karanikolaou did not grow up in a wealthy family. During her appearance on Call Her Daddy, she revealed that she and her sister, Alexia Karanikolaou, dealt with a “lot of commotion” when they were growing up.

Her mother struggled with addiction, she shared, which prompted the sisters to move around quite a lot and bounce between their dad’s home and those of several family members.

In June, the sisters announced in a joint Instagram post that their mother had died. “Heaven gained someone so special,” the girls wrote in the caption. “We’ll miss you everyday. We know you’re at peace now with papou… We love you to the moon & back forever.”

Karanikolaou, who is of Greek descent, also shared with Cooper that she financially supports her entire family as a result of the career she’s built for herself.

She met her BFF Kylie Jenner at age 13

Karanikolaou met her longtime best friend on a Friday night when the two were in middle school. A mutual friend connected them, she revealed during her Call Her Daddy interview, and they met at a Barnes & Noble in Calabasas, California. Rumors had long circulated that they met when Karanikolaou attended a fan event for Jenner, but she put that rumor to bed on the April 2022 podcast episode.

It was more than a year after they’d met that Karanikolaou and Jenner began being photographed together and dealing with paparazzi, which she described as a weird experience for the two teens.

Since meeting in 2010, the pair have become one of the internet’s favorite friendships, with Karanikolaou fitting seamlessly into the Kardashian clan and playing a major role in the life of Jenner's daughter, Stormi.

At one point this year, the friends had to clarify the nature of their tight friendship. Fans began theorizing that the two could possibly be in a romantic relationship after Jenner shared a photo locking lips with Karanikolaou on Valentine's Day and called her her "forever Valentine."

In the season 3 finale of The Kardashians on Hulu, the friends addressed the rumors. "Isn't it so funny that everyone thinks that we're dating these days?" Jenner said. "When we get a little alcohol in our system, we just like to kiss each other and stuff."

Karanikolaou called the speculation "weird," and Jenner joked that she "wished" she was "sexually attracted" to her bestie, noting that would "have been way easier."

She started her own alcohol brand, Sunny vodka, with friend Zack Bia

Karanikolaou and her birthday twin, DJ Zack Bia, have long been close friends, and last year they decided to take their friendship to the next level as they partnered on a new business venture together.

The duo launched Sunny vodka in March 2022.

“I have been working on this project with @zackbia for the past few years and we are so proud to share it with the world,” she wrote in an Instagram post the day the vodka brand launched. “We truly wanted to put our California spirit into this product and hope you all can feel the friendship and love with each sip.”

In August, Karanikolaou took a trip to Las Vegas’s Sugar Factory to promote the vodka in the busy city. She stepped behind the bar at the restaurant and poured several handmade co*cktails using the brand.

She's currently dating TikToker Jaden Hossler

Despite being on-again off-again for much of the beginning of the year, Karanikolaou is back together with TikToker Jaden Hossler.

The two first began teasing their relationship on social media in January, when Hossler was spotted on a getaway with her and her friends in Turks and Caicos.

In an Instagram post from the trip, he said, "I forgot that I forgot what it felt like to love life like this.” Karanikolaou commented on the post, "😊🤍."

In February, the pair went Instagram official with Hossler posting a gallery of selfies with his girlfriend where the two were cuddling.

By April, the couple had gone close to radio silent on social media in terms of posts of each other, and rumors circulated that they had split. While neither ever confirmed or denied a breakup, fans were excited to see them reunite this summer, and they’ve resumed their PDA-heavy social media presence.

They first reunited in July, appearing — and posing — together at an event launching Diesel’s collaboration with FWRD, but it wasn’t until August that they seemingly confirmed their status online.

On Aug. 3, the Sunny vodka co-founder shared a TikTok with Hossler using an audio of Kim Kardashian.

“Okay guys, we’re back. Did you miss us? Cause we missed you,” Kardashian said in the audio, which was used to promote the third season of Hulu’s The Kardashians.

Soon after, they showed their love for each other on Instagram, too. Hossler commented “bless the lord” on a selfie Karanikolaou posted showing off her new blonde ‘do on Aug. 8, and he was featured in a carousel of photos she posted from her sister’s baby shower the next week.

She has previously been linked to Noah Centineo, the Bachelorette's Tyler Cameron and Sammy Wilkinson.

She's got a circle of super famous friends

Though Jenner may be one of the friends she’s known the longest, Karanikolaou has a host of super famous friends in her circle.

From Sofia Richie to Hailey Bieber and Kendall Jenner, she boasts an impressive crew. Some of her tightest friends include fellow influencer and model Victoria Villarroel, who she's known since she was 15. Villarroel was Jenner's personal assistant for several years before joining the friend group — and her younger sister, Sofia Villarroel, is also often tagging along with the famous squad.

Carter Gregory, an A&R VP at Capitol Records and influencer in his own right, is another face that regularly spends time with Karanikolaou and Jenner's crew.

Wildflower Cases founder Devon Lee Carlson, singer Olivia O’Brien and Kelsey Calamine are among Karanikolaou’s other close friends.

Perhaps the most clarity about just how famous the Sunny vodka co-founder's circle really is came in 2021, when she participated in the then-viral FaceTime challenge. The TikTok challenge saw users call several of their contacts, tell them they're too buys to talk, and then hang up, as a prank. In Karanikolaou's video, she showed off an impressive roster of famous contacts.

Rappers Jack Harlow and Drake, along with Blake Griffin, Pete Davidson and Charlie Puth were among the famous faces Karanikolaou called during the one-minute video.

She's been very open about her cosmetic procedures

A standout feature about Karanikolaou has long been her photogenic physique. However, the internet personality has been open about what kinds of procedures she’s had done on her body to achieve the impressive results she often shares.

On her YouTube channel, she’s documented procedures from lip fillers and a breast lift in 2017 to an eventual reduction of her breast implants in 2019. She’s also always shared what surgeons she’s visited for the procedures she’s undergone — she’s cited Los Angeles-based Dr. Ghavami for several procedures, as well as Dr. Galanis for her 2019 breast implant reduction.

She's modeled for several major campaigns

Since stepping into the public eye, Karanikolaou has amassed an impressive social media following, and has turned that into an opportunity when it comes to modeling. Last year, she posed for Alexander Wang’s bodywear collection in what was arguably her biggest high-fashion shoot yet.

She also helmed a collection with Pretty Little Thing that launched in 2021, has modeled for Rihanna’s Savage x Fenty lingerie brand, and even collaborated with her bestie, Jenner, on a Kylie Cosmetics collection.

Jenner said she and her friend had “started dreaming of this collab a few years ago” in an Instagram post announcing the Stassie x Kylie collaboration, which included two liquid eyeliners, “a special stassie lipkit,” two sets of lipgloss and a “highlighter in stas’s perfect shade.”

“Making this collection with my best friend has been a dream and i hope you all love it as much as we do!!” Karanikolaou wrote on Instagram of the collaboration.

Aside from Kylie Cosmetics, the Sunny vodka founder has also posed for several of her other famous friends’ brands, including Khloé Kardashian’s Good American.