Rihanna, Kendall Jenner Feud Rumours: ASAP Rocky Allegedly Caught in Bitter Spat, Riri's Disdain Fuelled by Chris Brown Past

Rihanna is said to be locked in a years-long feud with Kendall Jenner, with insiders claiming in Los Angeles this week that ASAP Rocky now finds himself in an 'awkward situation' as the model allegedly keeps trying to contact her ex.

The rumoured Rihanna–Kendall Jenner tension, which reportedly dates back to the singer's turbulent history with Chris Brown, has re-emerged as sources insist the Fenty founder has warned Kendall to stay away from her partner.

Rihanna and ASAP Rocky made their relationship public in 2020 after years of friendship and speculation. They have since built what looks, from the outside, like a very settled family life, now sharing three children: RZA, 4, Riot, 2, and 8‑month‑old Rocki.

Rocky has previously described Rihanna as 'the love of my life,' and the pair have turned red carpets, fashion campaigns and even front‑row shows into a kind of rolling public romance. Set against that, whispers that an old flame is back in the picture — even just by text — land differently.

Feud Rumours Tied To Chris Brown Past

According to one source, Rihanna's dislike of Kendall did not begin with Rocky at all, but with Chris Brown. Rihanna dated Brown on and off between 2007 and 2013, a relationship overshadowed by the widely reported domestic violence incident in 2009. The insider claims that, around the period when Rihanna and Brown were reconciling and splitting again, 'Kendall was always all over Chris and now she's all over Rocky.'

It is a loaded allegation, and there is no public record of Kendall addressing it. Still, within this telling, the pattern matters. It paints Rihanna as 'super‑territorial' and irritated by what she apparently sees as a repeat of old behaviour. The same source says bluntly: 'Rihanna has not been shy about her disdain for Kendall. She is very dismissive of her.'

The supposed rivalry has a second layer. Before Rihanna and Rocky became a couple, Rocky and Kendall were briefly linked romantically.

The rapper, now 37, is said to have dated the model, 30, for about a year from 2016. Whatever that relationship was, it seems to loom large in the retelling. One insider insists Kendall still views Rocky as 'the one who got away,' a line that almost sounds too neat until you remember how often exes do end up mythologised this way in celebrity circles.

Rihanna, now 38 and a billionaire entrepreneur as well as a musician, is said to hate that history. The source claims she has effectively banned Rocky from being friends with Kendall, supposedly to draw a hard line under anything that came before their family.

ASAP Rocky Managing 'Awkward Situation' As Rumours Swirl

This is where ASAP Rocky, in these Rihanna and Kendall Jenner feud rumours, finds himself portrayed as the man in the middle. The insider says 'the problem is that Kendall won't take the hint,' alleging she continues to text him and attempt contact, seemingly 'oblivious to the drama she's causing for him at home.'

There is a harsher reading, too. The same source concedes another possibility, that Kendall 'just doesn't care how much chaos she causes.' That is a strong character sketch based entirely on an anonymous briefing. Without comment from Kendall or her representatives, it remains precisely that: a sketch, not a confirmed fact.

What is clearer, at least from the source's account, is where Rocky's loyalties are meant to lie. 'Rocky's loyalty is 100 per cent with Rihanna, but at the same time he does feel bad for Kendall,' the insider says, describing the situation as 'pretty awkward' for him. If pushed to choose, they add, 'he will have RiRi's back for sure.'

It is not hard to see why. The couple's public narrative has been unusually affectionate for a celebrity pairing of their stature. Rocky, never especially shy in front of a camera, is said to 'love every inch of her,' even enjoying watching other men 'drooling over her.' Instead of jealousy, the insider claims, he sees it as 'a flex' — proof of his own good fortune as much as hers.

There is an irony here that does not need spelling out. A man who reportedly takes pride in others' admiration for his partner is now cast as the reluctant recipient of attention from an ex, while that same partner is described as drawing strict boundaries. On one side, a fiercely guarded family unit; on the other, a persistent former connection and a decade‑old resentment involving Chris Brown.

What is missing so far is any official comment. Rihanna has not addressed the rumours publicly. Kendall has stayed silent. Representatives for ASAP Rocky have not responded on the record. Until they do, this remains a story pieced together from unnamed sources, conflicting loyalties and a long celebrity memory.