Kylie Jenner and Timothée Chalamet have officially stepped into the spotlight together, making their red carpet debut at the 70th David di Donatello Awards in Rome on May 7, 2025. The couple, who first sparked dating rumors during the 2023 Met Gala season, showcased their relationship in a more public manner, hand in hand and smiling for the cameras.
Chalamet was honored with the David for Cinematic Excellence for his work in film, a fitting accolade for the rising star. For the occasion, Jenner donned a sleek black floor-length gown with a plunging neckline from Schiaparelli’s Fall/Winter 2025 collection. She accessorized with a velvet clutch, surrealist gold earrings, and styled her hair in a slicked-back ballerina bun. Chalamet complemented her look in a double-breasted velvet suit, complete with a white rose pinned to the lapel and black dress shoes.
This moment marks a significant turn for the couple, who had previously kept their relationship mostly under wraps, apart from a few candid sightings and courtside appearances, including that viral kiss at the US Open. They were also recently spotted together at Coachella and the Miami Grand Prix. However, their coordinated appearance in Rome suggests a new chapter in their relationship, one that may involve more public outings.
Interestingly, Jenner attended the 2025 Met Gala solo just days before their red carpet debut in Rome. She wore a sculptural halter-neck gown with a sheer corset bodice by Ferragamo, showcasing a sharp contrast to her soft, Old Hollywood-inspired look from the previous year’s Met Gala, where she wore an ivory silk gown by Oscar de la Renta. According to PEOPLE, Chalamet opted to skip the fashion event to watch a New York Knicks basketball game against the Boston Celtics, revealing his loyalty to the team.
A source close to the couple shared with the Daily Mail that while Chalamet considered attending the Met Gala, he ultimately chose to prioritize his passion for basketball over the high-profile event. The insider noted, “If it was Kylie’s first Met Gala or an event where she was being honored for something, then he would have been there 100 percent, but they decided to do their own thing.”
Body language expert Judi James weighed in on the couple’s appearance in Rome, stating that Kylie “appears less clingy here and less inclined to work the pose as she has on most of their appearances together.” She observed that Kylie leaned back against Chalamet, who reciprocated with one hand around her torso, reflecting a sense of intimacy. James remarked that Kylie added an “approval gesture by placing her own hand on top of his and inclining her head backwards to look like a woman in love.”
While the couple’s relationship seems to be blossoming, they also maintain their personal space, as evidenced by their decisions surrounding the Met Gala. Jenner reportedly did not pressure Chalamet to accompany her to the event, allowing him to enjoy his own time. This mutual respect for each other’s interests is a key component of their relationship.
In a humorous twist, Jenner shared a behind-the-scenes clip on Instagram from the 2025 Met Gala, revealing a minor wardrobe malfunction. After the event, she struggled to remove her high heels, which had been glued to her feet. A team of assistants had to use a solvent to free her feet from the shoes. “Max told me to tape my feet in the shoe and now my feet are stuck in the shoes!” Jenner explained, tagging the Ferragamo creative director, Maximilian Davis. Despite the mishap, Jenner assured her fans that her feet survived the evening.
For the Met Gala, themed “Superfine: Tailoring Black Style,” Jenner opted for a stunning custom Ferragamo dress, featuring a sheer corset and a textured bra top with a matching skirt. She elevated her look with strappy patent leather pumps and diamond earrings by Lorraine Schwartz. However, she wasn’t the only one to experience a wardrobe hiccup at the gala. Her older sister Kim Kardashian also had an awkward moment when a security guard accidentally stepped on her Chrome Hearts skirt train.
As fans eagerly await more appearances from the couple, the red carpet debut at the David di Donatello Awards signals a potential shift in how Jenner and Chalamet choose to share their relationship with the public. Whether it’s a one-off moment or the start of a new era, their fans are hopeful for more coupled-up red carpet moments in the future.
With their relationship continuing to unfold, it’s clear that both Jenner and Chalamet are navigating their public personas while also cherishing their private moments. As they step into this new phase, fans can only anticipate what’s next for this dynamic couple.
