Born to A-list parents Will and Jada Pinkett Smith, Jaden was destined for stardom. And
like most people in Hollywood, there's been a lot of speculation about his love life over
the years. And now, as one of Tinseltown's most eligible twenty-somethings, let's just
say Jaden always keeps us guessing.
"I mean, I'm good at kissing, so…"
When it comes to setting the standard for Jaden's partners in life, his mom is seemingly
the one doing the measuring. Jada has even publicly admitted that she hasn't always been
a fan of the people her son has brought home. On her show "Red Table Talk," she revealed
that Jaden's dates sometimes made her feel worried while Willow's partners have been,
quote, "spectacular."
That being said, Jada's parenting philosophy seems to have always been that she lets Jaden
be Jaden. She said,
"You've got to go with the flow. Your kids aren't always going to date people that you
love, but I've learned that you really have to just be there and support, because [if
you don't] that can create a conflict that you can't get around."
"I felt as though I needed to jump on the journey with my kids, versus trying to dictate
the journey."
Fans know that Jaden is an LGBTQ+ fashion icon who loves to challenge gender norms.
And even though he often enjoys the company of women, when it comes to his love life,
anything is possible. He had that self-confidence even as a teen when he modeled for Louis Vuitton's
Spring/Summer 2016 womenswear campaign. He told Nylon that year,
"You just have to believe in yourself, you know. The world is going to keep bashing me
for whatever I do, and I'm going to keep not caring. I'm going to keep doing the same things
— I'm going to keep doing more things. […] The next generations of kids will all think that
certain things are normal that weren't expected before my time."
Jaden hung around lots of other celebrity kids growing up, including "Cory in the House"
star Madison Pettis. Back in 2011, it was rumored that the two young stars were even
dating. At the time, they were around 13 years old. They didn't have their driver's licenses
yet, so going to each other's birthday parties summed up their crushes on each other. Of
course, they weren't just regular birthdays with a homemade cake and a piñata in the
backyard. No — these were full-blown red carpet events. When Madison turned 13, she
held a blowout party at the Eden Club in Hollywood, where young Disney Channel celebs and other
up and coming tween stars of the industry stopped by to celebrate with the birthday
girl.
"Hey what's up it's Madison Pettis—"
"And Jaden Smith—"
"And we're at my 13th birthday party."
While this cute moment with the Disney star likely wasn't a major romance for Jaden since
they were both so young, it seems like Jaden has a type when it comes to dating in Hollywood;
other famous people. They likely have the shared experience of living in the spotlight,
so it might make it easier for him to relate to someone who understands what it's like
to be a famous kid.
It might be surprising to learn that Jaden often narrows down his dating life to not
only famous people, but to the younger siblings of famous people. It's a theme we see in his
early dating life when he dated Vanessa Hudgens' little sister, Stella Hudgens. It was probably
pretty easy to get to know Stella since she is friends with Jaden's little sis, Willow.
They reportedly dated in 2011 and broke up sometime in 2012, but the two likely bonded
over having famous siblings.
That being said, Stella is successful in her own right, having already appeared on TV shows
like "According to Jim" and "American Family." She also knows a thing or two about dating
other famous siblings; she once dated Dylan Efron — Zac Efron's younger brother. It
all just goes to prove how Jaden was pretty tight with that circle of famous, young stars.
It seems like they all knew each other and were all within six degrees of separation.
After Jaden split with Stella in 2012, he found his way to Sofia Richie, daughter of
Lionel Richie and younger sister to Nicole Richie. While their relationship was a flash
in the pan, their friendship has endured. Once Sofia and Scott Disick called it quits
in May 2020 after three years together, Jaden and Sofia were spotted hanging out together
in Malibu that September. And that's when the rumors started circulating. A source told
US Weekly,
"[They] only had eyes for each other. […] [They were] laughing and joking and looked very
intimate."
But leave it to Ryan Seacrest to try and get the real story about what happened over that
weekend because, according to Jaden, it was much ado about nothing. He explained to "On-Air
with Ryan Seacrest,"
"We've been going to the beach pretty consistently for 10 years too. Yeah, we're just homies,
and we love each other and it was fun."
It sounds like these two are securely planted in the friend zone, but there's something
comforting about a familiar face when you're going through a breakup.
The press went bananas when then 14-year-old Jaden Smith attended 17-year-old Kendall Jenner's
birthday party at an ice skating rink. A photo surfaced showing the two circling the rink
with their fingers intertwined in what looked like a very sweet moment — and that's why
Kendall had a lot of explaining to do. She gave a nonchalant answer to E! News in 2012
when she was asked about the photo, brushing it off with:
"Oh, you mean that picture! I didn't even see it. I don't remember, I swear. We were
holding hands with everyone. It's ice skating. I held Kylie's hand, too. […] He is like
my little brother. So funny. [I] never knew people talked about that."
The supermodel completely iced Jaden out, but it's understandable given that a three-year
age difference is a big deal when you're in your teens. The best part of the whole story
is that the paparazzi missed the real scoop that was right under their noses that night
— Jaden wasn't dating Kendall, he was actually dating her little sister.
In 2013, news broke that then 14-year-old Jaden was dating a 15-year-old Kylie Jenner.
A source told US Weekly,
"It's new, but they've been friends forever."
The young romance was seemingly a natural fit, considering the Smith kids grew up near
the Kardashian-Jenner gang, so their friendship ran deep. It was also at the height of "Keeping
Up with the Kardashians," so Jaden could likely easily relate to everything Kylie was going
through, growing up in the public eye. When he was asked about his blossoming relationship
with the future makeup mogul, he told "Hello!" magazine,
"She's one of my best friends. I was in LA, we were all hanging out. Then I went to New
York and she came too, then she came here and surprised me, so that's pretty baller."
The couple didn't last beyond 2014, but that's not the end of their story. When Kylie ended
her relationship with rapper Tyga for the first time in 2015, there were rumors going
around that Jaden had something to do with the breakup. A source dished to E! News,
"Kylie and Jaden have been hanging out lately and it made Tyga suspicious. He thought something
might be going on."
But hold up! Another insider swore that there was nothing going on, adding,
"Jaden though will always love Kylie and Kylie will always have a love for Jaden. They grew
up together and were each others' first loves."
If you want to win prom, you invite Jaden Smith to be your prom date. And that's exactly
what "Hunger Games" star Amandla Stenberg did when Jaden accompanied her to a dance
in 2015. He had already been experimenting with skirts and dresses earlier that spring
when he was photographed by the paparazzi. He tweeted about the incident, writing,
"That Moment When [You're] Wearing A Dress With No Pants And You Swerve Way [Too] Hard."
A month later, Jaden found a way to elevate his prom outfit, donning a skirt matched with
a black t-shirt and tuxedo jacket. Stenberg coordinated her look with his in a black gown
with metallic accents.
But that wasn't the only prom Jaden attended. He made sure to hit then-girlfriend and "Nashville"
star Odessa Adlon's prom in 2018. This time, in formal — designer — pants.
Remember when mom Jada said that she was worried about some of her son's significant others?
She might have been referring to Instagram star Sarah Snyder, who had a very high-profile
arrest while she was dating Jaden. According to US Weekly, the couple started dating in
early 2015, and they were spotted everywhere from the front row of New York Fashion Week
to nearly every street corner, where they found time to pack on a whole lot of PDA.
But in June of 2015, according to "Page Six:"
"[Snyder was] arrested and charged with one count of grand larceny in the third degree.
[…] [She was] accused of stealing a $15,995 Hermès purse from the Route 117 Bypass Shopping
Center [in New York.]"
But when it came to what Snyder had to say about it, she says she didn't do it. She explained
to "Harper's Bazaar,"
"There was a lot of proof I didn't do it. There was a time-stamped plane ticket, my
dad's affidavit, my phone records, my credit card statement, and there are pictures of
me in my dad's house in Florida on the same day they claim I stole the purse."
The charges were eventually dismissed in 2016, but the damage was done. That wasn't the situation
that ultimately made the couple split, though. It took cheating allegations to put their
love through the ringer after an Atlanta photographer posted a photo online of himself in bed with
Sarah, according to Hollywood Life. By 2017, the duo was dunzo, with a source telling "US
Weekly,"
"They had been on the rocks for a while and stopped having shared interests."
Jaden has created a lot of buzz around whether or not he's actually dating Tyler the Creator.
He has referred to the rapper as his "boyfriend," but at times, it seems to be no different
than a woman talking about one of her girlfriends — as in; a girl, who is a friend. Yet there
are often public professions of love that make fans think the two might be more than
just buds.
"I just like all his looks, honestly. He's just a vibe on every level."
In 2018, at Tyler's annual Camp Flog Gnaw festival in Los Angeles, Jaden stopped in
the middle of his set to let the audience in on a little secret, revealing,
"I just wanna say Tyler, the Creator is the best friend in the world. And I love him so
f---ing much. […] And I wanna tell you guys something, I wanna tell you, Tyler doesn't
wanna say, but Tyler is my motherf---ing boyfriend and he's been my motherf---ing boyfriend my
whole life."
But if you think Jaden just got caught up in the thrill of the moment, think again.
Jaden later stirred the pot by congratulating Tyler the Creator after he won a Grammy for
Best Rap Album for "Igor" in January 2020, when he tweeted:
"My Boyfriend Just Won A Grammy."
Maybe it's more than a friendship, maybe it's not…we may never know.
We have to remember that Jaden's work isn't done unless he's kept us all guessing about
his love life — and it's clearly never as simple as it seems. He and model Cara Delevingne
spent Valentine's Day together in 2021, which led people to speculate that their friendship
was now a budding romance. Like a perfect gentleman, Jaden brought Cara a bouquet of
red roses along with a friendly kiss.
"It's a date."
"It's not a date."
"Well it sure sounds like a date."
They starred in 2020's "Life in a Year" together, so they were likely pretty close thanks to
those circumstances. But did they take it to the next level on the most romantic day
of the year? It's honestly hard to tell because Delevingne has also been linked to Paris Jackson,
and we would have to sort through their relationship before ever figuring out Jaden and Delevingne.
Per usual, it's very much like Gen Z to keep us wondering who — if anyone — is dating each other.
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