The 7 Most WTF Moments Of Kylie Jenner And Jaden Smith’s Relationship

Jaden Smith and Kylie Jenner at Ender's Game premiere in LA October 2013

(Photo: Frederick M. Brown / Getty Images Entertainment)

Kylie Jenner and Jaden Smith have been rumored to be a couple for more than a year now, and although they’ve never confessed beyond friendship (as is the Jenner way), there have been plenty of weird moments to come out of their relationship. They individually come from two of the most WTF families in show business, so when you put them together odd things are bound to happen. And of course their parents won’t pay attention to a second of it.

Since their friendship/courtship/weirdship is being brought up again lately thanks to some scandalous photos, what better time to look back on the course of their time together and pick out a few of the most puzzling moments.

1. When they first hung out together in London.

Jaden Smith, Kylie Jenner

(Photo: Palace Lee / Pacific Coast News)

It was the beginning of a beautiful friendship/love affair/business arrangement, and it made us all go, “Huh? What? Okay, sure, I guess.”

2. When Jaden dressed up as Iron Man for a day out.

Jaden Smith as Iron Man with Kylie Jenner in New York May 2013


While out shopping with Kylie in New York, Jaden apparently bought an Iron Man costume — why wouldn’t he? — and felt the need to break it in that same day. You know, the usual.

3. When they kinda sorta professed their love for each other on Twitter.

Jaden replied to one of Kylie’s inspirational tweets earlier this year with the words “Okay I Love This Girl,” and then Kylie did the same for him. What kind of love? Platonic love? Love love? TELL US MORE!

4. When Jaden acted like a weirdo to Penelope Disick.

Jaden Smith Penelope Disick

(Photo: Instagram)

Sometimes Jaden hangs out with the rest of the Kardashian klan as well. And sometimes he has staring contests with Penelope Disick. Let’s hope he’s not trying to take her soul.

5. When they made crystals together.


(Photo: Instagram)

Kylie and Jaden have been hanging out with Jaden’s sister Willow and also a 20-year-old actor named Moises Arias. They’ve been making “orgonite” pyramids with muffin tins and posting photos on an Instagram page called the Orgonite Society which seeks to “Balance Gaia’s Energy.”

6. When they were rumored to be in a cult.

Willow Smith Osho book Instagram(Photo: Instagram)

The kids are apparently reading up on Bhagwan Shree Rajneesh, also called Osho, who was sometimes known as “the sex guru,” expressed homophobic beliefs, and whose followers committed a bioterror attack in Oregon. There’s Willow holding one of his books.

7. When they posed in bed together.

Jaden Smith Kylie Jenner shirtless bed Tumblr 2014

(Photo: Tumblr)

Their hangout sessions with Moises Arias also involve sitting around in bed with some clothes missing. Willow caused controversy when she was photographed with Moises himself, and soon after people started talking about Jaden and Kylie’s version.

You can reach this post's author, Jill O’Rourke, on twitter.
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    • Alexis Rhiannon

      Oh y’know, just making crystals.

      • Alyssa

        Super caj. Nbd

    • markmywords

      LOL@ #2. Reg #4 he’s an immature boy and boys do stupid stuff with infants. And #6 is probably a PR gag as they haven’t been in the headlines for … how long? I can’t help myself, my gaydar lightens up for Will jr. and Kendall excersises beard-dom (is that a word?) to follow in her sister’s footsteps. I have yet to see a picture of both where they have more than zero chemistry.

    • happy1ga

      I’m not sure you can be in a secondary cult if you’re already a Scientology cult member…? I guess I was unaware you could have tiered cultery levlels lol. Not that it matters, they have been brought up under the church’s belief that children make their own decisions as adults, and I don’t see it stopping this late in the game, and PMK’s second stringers travel the globe sans supervision or education,…match made in Hollyweird.

    • mich_nicole

      uh…isnt that a weed leaf on the blanket and they are how old?

    • Un Feuille Bleu

      1-These are not “WTF” things. These are normal, uninteresting events
      2-The writer of this “article” seems to be an adult, but is writing about/presumably stalking a 15 year old couple. That is the only “WTF” thing about this post.