Inside Jaden Smith's Complicated Love Life

Jaden Smith has been famous since the day he was born. With A-list parents Will Smith and Jada Pinkett Smith, he was bound for stardom in one way or another. He made his film debut in 2006 alongside his father in "The Pursuit of Happyness," but it was thanks to the 2010 reboot of "The Karate Kid" that the world fell in love with him.

While he's continued to work in the entertainment industry, there's been a lot of curiosity about his love life over the years. And let's just say it's never boring because Jaden always keeps fans guessing. He's not a celebrity who likes to follow the rules. In fact, he's always been someone who marches to the beat of his own drum — exactly how his dad raised him.

"What I do with my children, that I feel that the greatest gift that I can give my children is the freedom to be who they are," Will told BET. "Jada and I are very serious about finding what they are and encouraging them to be what they are because you can never be happy being what you're not." That philosophy has seemingly carried over into Jaden's private life, where he finds comfort in dating other famous people. However, he hasn't tied himself to one person just yet. Jaden seems to be having fun as a single guy in Hollywood, which means sometimes things get complicated.

Keep scrolling to find out what you need to know about Jaden Smith's love life.

When it comes to setting the standard for Jaden Smith's love life, his mom is seemingly the one doing the measuring. Jada Pinkett Smith has publicly admitted that she hasn't always been a fan of some of the people her son's brought home. On her Facebook Watch talk show "Red Table Talk," Jada revealed that a few of Jaden's dates made her feel "concerned" while Jaden's sister Willow Smith's significant others have been "been spectacular, in all honesty."

That being said, Jada isn't interested in pushing her son away, so she knows that she has to let Jaden be Jaden. "You've got to go with the flow," she explained on her talk show. "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."

Anyone who dates Jaden Smith has to know that he is an LGBTQ+ fashion icon who loves to challenge gender norms. This helps him keep an air of mystery around who he is dating. And even though he often enjoys the company of women, he's making sure fans know that anything is possible. He's seemingly had that self-confidence even as a teen when he modeled for Louis Vuitton's Spring/Summer 2016 womenswear campaign. Sporting a leather jacket accessorized with a pleated skirt and crocheted top, Jaden was happy to rock whatever fit his flair for fashion.

"You just have to believe in yourself, you know," he said in his 2016 Nylon cover story. "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." He's added that he's fine "taking the brunt of" any bullying that might happen so that "the next generations of kids will all think that certain things are normal that weren't expected before my time."

It seems that Will Smith and Jada Pinkett Smith did a great job instilling that sense of pride in their son, but how does it carry over to his dating life? Well, when he first started dating, it was like most teen romances — puppy love — but as he's gotten older, he's definitely pushed the boundaries.

Jaden Smith hung around lots of celebrity kids growing up, including "Cory in the House" star Madison Pettis. Back in 2011, it was rumored that the two young stars dated. At the time, they were around 13 years old. It's worth mentioning that there's not really a lot to do at that age. They didn't have their driver's licenses yet, so going to each other's birthday parties seemingly summed up their young, romantic lives. Of course, they weren't just regular birthday celebrations with a cake that mom made and a few games in the backyard — these were full-blown public events.

When Madison turned 13 years old, she had a big party at the Eden Club in Hollywood, where young Disney Channel celebs like Roshon Fegan of "Shake it Up" fame and former Disney darling China McClain stopped by. The paparazzi were on hand to mark the festivities on the red carpet and beyond.

While this cute moment with the Disney star likely wasn't a major romance for him 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 a shared experience of being in the spotlight, so it might make it easier for him to date someone who understands what it's like to be Will Smith's kid.

It might be surprising to learn that Jaden Smith 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 Smith. They reportedly dated in 2011 and broke up sometime in 2012, but the two likely bonded over having famous siblings — Willow and Vanessa are both pretty major all on their own.

That being said, Stella is successful in her own right, having appeared on TV shows like "According to Jim" and "American Family." She also knows a thing or two about dating other famous siblings, as, at one point, she dated Dylan Efron (a.k.a. Zac Efron's younger brother). Oh, what a tangled web Hollywood loves to weave, so you can see how Jaden was pretty tight with that circle of famous, young stars. It seems like they all knew each other and they were all within six degrees of separation.

After Jaden Smith split with Stella Hudgens in 2012, he found his way to Sofia Richie, daughter of Lionel Richie and younger sister to Nicole Richie. While their relationship seemingly didn't last, their friendship has endured. After she and Scott Disick called it quits in May 2020 after three years together, Jaden and Sofia were spotted hanging out together in Malibu, Calif. in September 2020. That's when the rumors started circulating.

A source told US Weekly that the two young celebs "only had eyes for each other" as they were seen "laughing and joking and looked very intimate" while enjoying their day at the beach. They continued their Labor Day weekend outing with a trip to the very Los Angeles hotspot Nobu Malibu with another couple.

But leave it to Ryan Seacrest to try and get the real story about what happened over that holiday weekend because, according to Jaden, it was much ado about nothing. "We've been going to the beach pretty consistently for 10 years too," he said on iHeartRadio's "On-Air with Ryan Seacrest". "Yeah, we're just homies, and we love each other and it was fun."

It sounds like they are in the friend zone, but there's something comforting about a familiar face when you're going through a breakup.

The media got very excited when then 14-year-old Jaden Smith attended 17-year-old Kendall Jenner's birthday party at the ice skating rink. A photo surfaced showing the two circling the rink with their fingers intertwined in what looked like a very romantic 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."Oh, you mean that picture!" Kendall said. "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." Kendall supposedly had no idea that fans and the press were even speculating about their dating status. "He is like my little brother," she continued. "So funny. Never knew people talked about that." 

The supermodel completely iced him 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 dating her little sister, Kylie Jenner. We weren't kidding when we said Jaden really seems to like dating famous little sisters.

In 2013, news broke that then 14-year-old Jaden Smith 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 as the Kardashian-Jenner family grew up near the Smith family, so their friendship ran deep. It was also at the height of the KarJenners "Keeping Up with the Kardashians" fame, so Jaden could likely easily relate to everything Kylie was going through having grown up in the public eye. When he was asked about his blossoming relationship with the future makeup mogul, he gave the most enthusiastic answer to Hello! magazine, calling it "pretty awesome."

"She's one of my best friends," Jaden added. "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 some rumors going around that Jaden had something to do with the breakup. "Kylie and Jaden have been hanging out lately and it made Tyga suspicious. He thought something might be going on," one source told E! News. But hold up! Another insider swore that "nothing romantic has happened with them since she has been with Tyga."

"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" the second source said.

If you want to win prom, you invite Jaden Smith as your prom date. That's exactly what "The Hunger Games" star Amandla Stenberg did when Jaden accompanied her to a dance in 2015. He had already been experimenting with dresses earlier that spring when he was photographed by the paparazzi wearing a black dress with a white cami over it and accessorized with black Nike sneakers and leopard socks. He tweeted about the moment, writing, "That Moment When Your Wearing A Dress With No Pants And You Swerve Way to Hard (sic)."

A month later, Jaden found a way to elevate his prom outfit, donning a beige skirt matched with a black t-shirt and tuxedo jacket. He wore black leggings under the skirt and made sure to keep it comfy with his black sneakers. Stenberg coordinated her look with his in a black gown with metallic accents. It was a very sophisticated look for a high school prom — not a single dyed shoe or puffy sleeve in sight.

That wasn't the only prom he attended because Jaden made sure to hit then-girlfriend and "Nashville" star Odessa Adlon's prom in 2018, where he chose a modernized version of a very traditional look. Jaden sported a Louis Vuitton tux with silver threads on the sides of his pants. Odessa shimmered in a black-fringed skirt with a crop top and the ultimate prom accessory — a pink wrist corsage. Their glamorous look was captured at the end of the night with a tweet shared by Jaden who captioned the photo, "We Went To Prom, This Picture Describes The Experience."

Remember when Jada Pinkett Smith said on "Red Table Talk" that she was "concerned" about some of Jaden Smith's significant others? She might have been referring to Instagram-famous star Sarah Snyder, who had a very high-profile arrest while she was dating Jaden. Per US Weekly, the couple started dating in early 2015, and they were spotted everywhere from the front row of New York Fashion Week to every street corner, where they found time to engage in lots of PDA.

According to Page Six, in June 2015, Synder was "arrested ... and charged with one count of grand larceny in the third degree." Per the outlet, she was "accused of stealing a $15,995 Hermès purse from the Route 117 Bypass Shopping Center" in New York.

"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," she told "Harper's Bazaar" in 2016. The charges were eventually dismissed in 2016, but the damage was done. 

That wasn't the situation that broke her and Jaden up, though. It took cheating allegations to put their love through a major test after Atlanta photographer Gunner Stahl posted a photo online of him laying in bed with Sarah, per Hollywood Life. By 2017, the duo was dunzo and a source told "US Weekly," "They had been on the rocks for a while and stopped having shared interests."

Jaden Smith has confused a lot of people as to whether or not he's 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 their girlfriend — a girl, who is a friend. Yet there are often these public professions of love that make fans think the two have a romantic relationship.

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. "I just wanna say Tyler, the Creator is the best friend in the world. And I love him so f**king much," he said (via Newsweek). "And I love him so f**king much. and I wanna tell you guys something, I wanna tell you, Tyler doesn't wanna say, but Tyler is my mother f**king boyfriend and he's been my motherf**king boyfriend my whole life."

If you think that was a one-time thing, think again. Jaden stirred the pot again by congratulating Tyler the Creator after he won a Grammy for Best Rap Album for "Igor" in January 2020. "My Boyfriend Just Won A Grammy," he tweeted. So, maybe it's more than a friendship?

All that being said, we have to remember that Jaden Smith's work isn't done unless he's kept us all guessing about his love life because it's never as simple as it seems. He and model Cara Delevingne spent Valentine's Day 2021 together, which led to people speculating that their friendship was now a budding romance. Like the perfect gentleman that he is, Jaden gave her a bouquet of red roses and a friendly kiss. 

They starred together in the 2020 movie "Life in a Year," so they were likely pretty close to begin with, 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, who identifies as bisexual, has also been linked to Paris Jackson, and we would have to sort through their relationship before ever figuring out Jaden and Delevingne. So, it's very much like Gen Z to keep us wondering who — if anyone — is dating each other.