> At a Glance
> – Gwyneth Paltrow and Leonardo DiCaprio posed together at the AFI Awards on Jan. 9, 2026-three decades after she turned down his teenage advances.
> – In a 2023 podcast, Paltrow revealed DiCaprio asked her out when he was 19 and she was 21; she declined, saying he was “very loose with the goods.”
> – Today, Paltrow is married to Brad Falchuk; DiCaprio is dating Vittoria Ceretti, 27.
> – Why it matters: The photo marks a rare public reunion of two ’90s icons whose early dating history has long fascinated fans.
Three decades after a teenage Leonardo DiCaprio struck out with Gwyneth Paltrow, the Oscar winners flashed smiles for photographers at the AFI Awards in Los Angeles.
The 1994 Ask-Out
Paltrow first shared the decades-old story on the Call Her Daddy podcast in May 2023.
> “Nope, never made out with Leo,” she told host Alex Cooper. “He tried back in the day. But he was already like, you know, he was very loose with the goods from when he was 19.”
A February 1994 snapshot of the pair at the National Board of Review Awards in New York shows a 21-year-old Paltrow alongside a 19-year-old DiCaprio.
Where They Stand Now
- Paltrow, 53, wed Brad Falchuk in 2018 and co-parents Apple, 21, and Moses, 18, with ex-husband Chris Martin.
- DiCaprio, 51, has been linked to Italian model Vittoria Ceretti, 27, since August 2023; the couple rang in 2026 on a St. Barths yacht with Tom Brady.
Ceretti, in the April 2025 Vogue France cover story, said dating someone of DiCaprio’s fame “is something you learn,” adding, “If what you’re experiencing is real … love protects and gives confidence.”
Key Takeaways
- First joint photo since the ’90s, proving time heals all youthful rejections.
- Both stars arrived at the Jan. 9 gala with their current partners, underscoring the friendly nature of the reunion.
- The brief encounter offers a nostalgic nod for fans who followed their early careers.
