Kendall Jenner and Leonardo DiCaprio: Dating Rumors Explained
Kendall Jenner and Leonardo DiCaprio have never been a couple — but try telling that to the internet. The supermodel and the Oscar-winning actor keep turning up at the same exclusive parties, from a sunrise Art Basel afterparty in Miami to a Venetian wedding celebration, and every shared photo sends the rumor mill spinning again. Here is what actually connects them, what the sightings were, and why the dating rumors never turned into anything real.
| Who They Are | Kendall Jenner — supermodel and The Kardashians star. Leonardo DiCaprio — Oscar-winning actor (Titanic, The Revenant). |
| Relationship | Never dated — acquaintances who move in the same elite Hollywood party circles. |
| Known Sightings | Art Basel Miami (Dec 2019) at club E11EVEN; Jeff Bezos–Lauren Sánchez wedding celebrations, Venice (2025). |
| Current Status | No romantic link — DiCaprio linked with Vittoria Ceretti; Jenner most recently linked with Bad Bunny and Jacob Elordi. |
Table of Contents
Who Is Kendall Jenner?
Kendall Jenner, born in 1995, is an American supermodel and television personality who rose to fame on Keeping Up with the Kardashians before becoming one of the highest-paid models in the world, walking for Chanel, Givenchy, and Victoria’s Secret. She founded the 818 Tequila brand and stars on Hulu’s The Kardashians. Her dating life has been closely watched: past relationships include NBA star Devin Booker and rapper Bad Bunny, and she has more recently been linked with actor Jacob Elordi.
Who Is Leonardo DiCaprio?
Leonardo DiCaprio, born in 1974, is one of Hollywood’s most acclaimed actors, famous for Titanic, Inception, The Wolf of Wall Street, and his Oscar-winning turn in The Revenant (2015). Beyond acting, he is a prominent environmental activist through the Leonardo DiCaprio Foundation. His dating life is tabloid legend — a long string of model girlfriends including Gisele Bündchen, Bar Refaeli, and Camila Morrone. In recent years he has been linked with Italian model Vittoria Ceretti, with the pair reported together at the 2026 Academy Awards.
Kendall Jenner and Leonardo DiCaprio: Rumor Timeline
December 2019 — Art Basel Miami. The sighting that fuels most of the rumors. DiCaprio partied until sunrise after Art Basel Miami’s VIP preview, arriving at megaclub E11EVEN around 4:30 a.m. Inside, according to Us Weekly and Page Six reporting, he shared a table with Kendall Jenner, Gigi Hadid, and Bella Hadid — roughly 30 to 50 people in the group — until about 6 a.m. Notably, DiCaprio was dating Camila Morrone at the time, and there was never any suggestion of a hookup: it was a big-table party night, the kind both stars do routinely.
2016 — Cannes gossip. Tabloid outlets including OK! Magazine claimed DiCaprio and Jenner flirted at Cannes Festival parties. The story was never corroborated by any credible outlet and is widely regarded as unverified gossip.
2025 — Venice wedding celebrations. Both stars were among the dozens of celebrities in Venice, Italy, for Jeff Bezos and Lauren Sánchez’s wedding festivities — another shared guest list, not a date.
The pattern is consistent: same rooms, same guest lists, zero evidence of romance.
Are Kendall Jenner and Leonardo DiCaprio Dating?
No — Kendall Jenner and Leonardo DiCaprio are not dating and never have been, as far as any credible reporting shows. They are simply two A-listers who orbit the same ultra-exclusive social scene: Art Basel, Cannes, fashion weeks, and billionaire weddings. DiCaprio has been linked with Vittoria Ceretti in recent years, while Jenner’s recent headlines have centered on Bad Bunny, Devin Booker, and Jacob Elordi. The “romance” exists only in recycled photos and tabloid headlines that resurface every time an old party picture makes the rounds on social media.
Frequently Asked Questions
Did Kendall Jenner and Leonardo DiCaprio ever date?
No. Despite years of rumors, no credible outlet has ever reported them as a couple. Their connection is limited to shared appearances at major celebrity events.
When were Kendall Jenner and Leonardo DiCaprio spotted together?
Most notably at Art Basel Miami in December 2019, when they partied at the same table at club E11EVEN until around 6 a.m., alongside Gigi and Bella Hadid. Both also attended the Bezos–Sánchez wedding celebrations in Venice in 2025.
Was Leonardo DiCaprio flirting with Kendall Jenner at Cannes?
A 2016 tabloid report claimed flirting at Cannes parties, but it was never verified by reputable outlets and should be treated as gossip.
Who is Leonardo DiCaprio dating now?
He has most recently been linked with Italian model Vittoria Ceretti, with reports of joint appearances including the 2026 Academy Awards.
Who is Kendall Jenner dating now?
Her most recent widely reported relationships were with Bad Bunny and, before that, Devin Booker; she has also been linked with actor Jacob Elordi.
Why do people think Kendall Jenner and Leonardo DiCaprio are together?
Old party photos keep recirculating on social media without dates or context, and both are such famous faces that any shared frame sparks speculation.
Kendall Jenner and Leonardo DiCaprio are the perfect example of how the celebrity rumor mill works: put two famous, attractive single-ish people at the same table long enough, and the internet will write the love story itself. The real story is simpler — two stars, one social circle, and no romance at all.
