Jenner was also adding fuel to the rumours through cryptic Instagram story posts on that same night, including references to two Tyler, the Creator songs – "I Don't Love You Anymore" as well as lyrics to "Puppet" which includes the line: "I wanna call you and talk."
There was also reportedly a "tall, supersexy brunette" with Simmons' crew, according to sources.
In the interview with Vogue Australia, Jenner explained why she kept her relationship with the Philadelphia 76ers guard low-profile.
"I'm very young and right now I feel like relationships aren't always super-certain and I don't want to bring too much attention to something if you don't really know long term (that it's going to be)," she said.
"A relationship is only meant to be between two people, and the second you make it the world's business is when it starts messing with the two people mentally. Like once everyone is let in, you're letting all these opinions into your relationships, and I don't think that's fair."