Kylie Jenner is keeping up with the behind-the-scenes updates. Shortly after the Kardashians star made her red carpet debut with boyfriend Timothée Chalamet in Rome May 7, she gave a peek into the moments leading up to their relationship milestone. In selfies shared to her Instagram Story, Kylie posed in the black spaghetti strap maxi dress she wore on the carpet and showed off the unique gold earring in the shape of a hand she wore draped over her right ear. The 27-year-old also called out an unwelcome blemish on her face, writing atop the snap, “I have a new pimple friend that wanted to hang tonight.” In addition to a clip of herself posing on a balcony in Italy, the Kylie Cosmetics founder-who shares kids Stormi, 7, and Aire, 3, with ex Travis Scott-shared another selfie noting that she “did my own makeup tonight.” As for where Kylie and Timothée-who were first linked in 2023-headed to in the Eternal City? The pair attended the 70th David Di Donatello film awards ceremony, where Timothée was set to be honored with an award for Cinematic Excellence. During the event, Kylie and the two-time Oscar nominee were all smiles as they posed together in photos while donning coordinating looks. To complement Kylie’s black semi-sheer dress, Timothée sported an all-black suit and matching button-down underneath. He also donned a white rose corsage as he wrapped his arm around Kylie’s waist. Ahead of their relationship milestone, the pair shared a PDA-filled outing at a Los Angeles Lakers basketball game in April. In keeping with their sports fandom, Kylie and Timothée attended the Indian Wells tennis tournament in March and exchanged multiple sweet kisses during their tennis date. And just one week before, the couple packed on the PDA at the 2025 Oscars ceremony on March 2, as well as the Vanity Fair Oscars party that followed.