In their feelings? Kylie Jenner and Drake have been sparking dating rumors ever since they were spotted cozying up at his star-studded birthday party on October 23. Despite their recent encounter, the two have been “flirting for years,” a source exclusively told In Touch.

Kylie, 22, and Drake, 33,  have been in each other’s company for a while now, leading us to wonder how they linked up. Starting in August 2013, the two started rolling with the same crowd and the rapper even took the stage at Kylie’s epic Sweet 16 bash. Just a few years later, Drake attended the famous Kardashian-Jenner Christmas party in 2015, and thereafter celebrated the New Year with Kylie and Kendall Jenner in 2018.

The two kept things on the DL and at one point, they had been sneaking off together. “Back in early March, the two had a top-secret dinner date at a trendy Hollywood restaurant and were all over each other,” a source exclusively told In Touch. “They nearly became an item eight months ago.”

As for where these two stand today, it looks like things are starting to heat up. “Kylie and Drake’s friendship did take a romantic turn recently,” a source told Us Weekly. “At his Halloween party, they were affectionate and clearly there together. They’ve been seeing each other romantically. He also showed up to Kendall’s birthday.”

How Did Kylie Jenner Meet Drake

While attending Drake’s birthday party, the pair “spent a lot of time talking with one another,” an onlooker dished. “They seemed to be enjoying each other’s company. They were joking around, and Kylie was laughing. There seemed to be an attraction there.” Not only do these two seem to have a bond, but her famous fam totally approves. “Her mom and sisters are encouraging the romance,” the insider shared.

The billionaire recently split from baby daddy Travis Scott back in October, but she assured us there is no bad blood. “Travis and I are on great terms, and our main focus right now is Stormi!!” she wrote on Twitter on October 3. “Our friendship and our daughter is priority.”

Although the parents of 20-month-old Stormi seemed just peachy at Travis’ premiere for his documentary, Look Mom I Can Fly, back in August. But the couple were allegedly on the rocks. “Kylie has serious issues. She has her own life and career and child and can’t watch over him,” the insider exclusively told In Touch. “She is the billionaire megastar, and she feels so insecure about herself because of her relationship. They’ve had major trust issues from the start.”

Drake has been linked to some high-profile ladies but no one quite like Kylie. Looks like they were at the right place at the right time. For more on this story, pick up the latest issue of In Touch Weekly, on newsstands now!

Have a tip? Send it to us! Email In Touch at