Wait. Did they actually?
That’s the question that still haunts the deep corners of Reddit threads and the "explore" pages of anyone who lived through the mid-2010s. If you search for Kylie Jenner and ASAP Rocky, you’ll find a mess of grainy paparazzi photos, "insider" quotes from 2015, and enough Coachella rumors to fill a desert. But the truth is way more nuanced than a simple "yes" or "no."
The reality? They were never a thing. At least, not in the way the internet wanted them to be.
The Night Everything Blew Up (November 2015)
The internet has a very short memory until it doesn't. Back in November 2015, the world was convinced Kylie and her then-boyfriend Tyga were over for good. It was Tyga’s 26th birthday, and Kylie was conspicuously absent from the festivities. Instead, she was spotted at Hyde Sunset Kitchen in West Hollywood.
She didn't leave alone.
Cameras caught Kylie exiting the club at 2 a.m. with Ian Connor, a member of the ASAP Mob. They hopped into a black SUV. Sitting in the back seat, waiting for them? Lord Flacko himself. ASAP Rocky.
The headlines wrote themselves. "Kylie Moves On With Rocky!" "Tyga Replaced!" It was the perfect storm of drama. But here’s the kicker: they were just friends. Or, more accurately, they were part of the same hyper-connected, high-fashion social circle that defines the LA elite. Rocky was already becoming a fixture in the Kardashian-Jenner orbit, but he wasn't looking at Kylie.
He was looking at her sister.
The Kendall Confusion
This is where the Kylie Jenner and ASAP Rocky narrative gets tangled. For nearly two years, from 2016 to 2017, Rocky was heavily linked to Kendall Jenner. They were "very, very cozy" at Coachella (a recurring theme for this crew). They were spotted at the Met Gala. They did the "not-quite-confirming-but-definitely-dating" dance for a long time.
Because Rocky was dating Kendall, he was constantly around Kylie. He was at Kylie’s 19th birthday party. He was at the family dinners. If you see a photo of them together from 2017, chances are Kendall is just out of frame or they’re literally just hanging out as future-maybe-in-laws.
The confusion stems from the fact that the Kardashian sisters often share the same social space. In 2015, when those first "dating" rumors sparked, Rocky was likely just a bridge between worlds. He represents the intersection of Harlem street style and high-fashion luxury—a vibe that the Jenners were desperate to co-opt at the time.
Coachella 2017: The Real Turning Point
People often cite Coachella 2017 as a big moment for Kylie Jenner and ASAP Rocky, but for the exact opposite reason they think. This was the weekend the "Kylie and Rocky" rumors died and the "Kylie and Travis Scott" era began.
While Kendall was getting "all over each other" with Rocky at the WeedMaps party, Kylie was busy meeting the man who would eventually become the father of her two children. Travis Scott was performing, Kylie was there, and as she famously told GQ, they basically rode off into the sunset on his tour bus immediately after.
It’s wild how close these timelines are. One sister was with Rocky; the other was starting a life with Travis. Because both men are titans of the same industry, they are constantly compared, which keeps the Rocky-Kylie search queries alive.
The "Gross Shoutout" and the Falling Out?
There was a weird moment in 2017 where things got a bit... awkward. Rocky released a track where he mentioned Kylie in a way that wasn't exactly flattering. It wasn't a "diss" per se, but it was the kind of name-drop that makes a friendship dinner a little tense.
Despite that, they’ve remained "industry friendly." You’ll still see them at the same Paris Fashion Week shows in 2026. Rocky is now firmly settled with Rihanna—they’re basically the royal family of music at this point—and Kylie has moved into her "quiet luxury" era with Timothée Chalamet.
Honestly, the idea of Kylie Jenner and ASAP Rocky as a couple feels like a fever dream from a different lifetime. It was a byproduct of a time when every paparazzi flash meant a new relationship.
Where They Are Now (2026 Update)
If you’re looking for a romantic connection today, you won't find one. Here is the current state of play:
- ASAP Rocky: He and Rihanna are the blueprint. They’ve welcomed three children as of 2025 and are currently navigating the world as a certified power couple. Rocky’s focus is on his creative agency, AWGE, and his upcoming film projects.
- Kylie Jenner: She’s been in a steady, surprisingly private relationship with Timothée Chalamet for nearly three years. Gone are the days of "King Kylie" and the rapper-boyfriend aesthetic. She’s focused on Khy and her beverage brand, Sprinter.
The two occasionally cross paths at Kanye’s Sunday Service or high-end fashion events, but the vibe is strictly "old acquaintances."
The Actionable Truth
So, what should you actually take away from the Kylie Jenner and ASAP Rocky saga?
- Don't trust 2 a.m. SUV photos. Just because two celebrities leave a club in the same car doesn't mean they’re dating. Usually, it just means they have the same security team or were heading to the same afterparty.
- Context is everything. Most "Kylie and Rocky" sightings were actually "Kendall and Rocky" sightings where Kylie happened to be present.
- The "Type" Myth. People love to say Kylie has a "type" (rappers), but her long-term relationship with Chalamet proves that people evolve.
If you're tracking their history, look at the dates. Anything from 2015 was a brief hangout; anything from 2016-2017 was likely related to Kendall. After that, they moved in completely different directions.
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Stop checking the 2015 archives. The real story is how they both ended up with the "loves of their lives" in completely different circles. Rocky found his match in a musical peer (Rihanna), and Kylie found hers in a Hollywood darling (Timothée).
Next time you see a "Throwback" post claiming they dated, you can safely call it out. They were just two people at the center of the world at the same time. Nothing more, nothing less.