Inside Kylie Jenner and Drake’s ‘Flirty’ Halloween Date

If reports are true, there’s something happening between Kylie Jenner and Drake. The influencers sparked romance rumors in mid-October after they were allegedly seen getting close at an event, and they’ve since kicked the rumor mill into overdrive after reportedly spending Halloween together.

As of writing, neither of them has commented on the alleged outing. However, sources detailed it in a new report, claiming that Jenner and Drake were being seriously “flirty.”

Kylie Jenner at an award show
Kylie Jenner at an award show | Photo by Dia Dipasupil/Getty Images for MTV

A closer look at how Jenner and Drake celebrated Halloween

E! News reports that the Scorpion rapper threw a star-studded party on Oct. 31 at the West Hollywood club, Delilah, where he and Jenner allegedly hung out “all night.” Jenner reportedly showed up after throwing a shindig of her own for her daughter, Stormi, whom she shares with Travis Scott. She and Scott separated in September following a two-year relationship.

“Drake was having a great time at his party at Delilah, he even brought his dad among his whole entourage. Kylie, Rob [Kardashian] and Stassie [Karanikolaou] were there too,” a source told E! News. “They went back and forth between the private bar area and the main area and they were sitting together at points and hanging out all night. It looked flirty. At the end of the night, Drake had a couple SUVs and he left at the same time as Kylie.”

“The whole crew migrated to Delilah [after Kylie’s bash] for an after-party and were in and out of the private room,” a second source explained to the outlet. “They had several tables designated to the party and were all there partying past 2 a.m.”

An insider noted that the partygoers grubbed on foods like chicken tenders and sliders and sipped on drinks such as vodka, tequila, and champagne while listening to hip hop tunes.

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It’s at least the second time Jenner and Drake have linked

The first time happened just over a week ago.

On Oct. 23, Drake had a celebration in honor of his 33rd birthday, with Jenner in attendance. Sources also noted that the two had spent a lot of time together during the event.

“She spent the most time near Drake and his friends,” an insider dished to Us Weekly. “Kylie was rapping to songs and dancing with her friends while she was next to Drake, but they weren’t dancing together, they seemed to have a connection though.”

Another source added, “They seemed to be enjoying each other’s company. They were joking around and Kylie was laughing. She seemed to be really happy and in a great mood and her and Drake seemed very comfortable with each other. There seemed to be an attraction there.”

The news came as a shock to many — including Scott, apparently. A source added to Hollywood Life that the ASTROWORLD rapper would feel “betrayed” if Jenner and Drake started dating, explaining that Scott sees Drake as a “good friend.”

Their relationship dates back to at least 2015 when they collaborated on the song, “Company,” from Drake’s album, If You’re Reading This It’s Too Late. Their most recent collaboration is the 2018 hit single, “SICKO MODE,” from Scott’s critically-acclaimed album, ASTROWORLD.

But you should probably take this all with a grain of salt because sources have also claimed that there’s still a chance Jenner and Scott will reconcile. Reports say that they still love each other and are often with each other due to their daughter. So, who knows what will really happen.