Drake Dating Kylie Jenner Is Really Awkward for Several Reasons

Kylie Jenner is living her best life. The young entrepreneur is going into 2020 as a billionaire, a mother, and the star of one of the popular reality TV shows of all time.

Jenner isn’t letting the grass grow under her feet following her recent breakup from Travis Scott, the father of her young daughter Stormi Webster. There have been several reports about Jenner and the rapper Drake getting romantically involved. Keep reading to learn about how the romance rumors started, how long Kylie Jenner has known Drake, and whether or not there is any truth to the rumors.

Kylie Jenner and Drake hung out at his birthday party

The hookup rumors began in October 2019, a few weeks after Jenner broke up with Travis Scott. Jenner attended Drake’s star-studded birthday party, and party-goers noted that the two superstars definitely had chemistry, going so far as to describe a “connection” between them.

Only a few days after the birthday party, they went to the same Halloween function and spent some time with each other.

Some sources have claimed that Drake has always “had a thing” for the much-younger Jenner and that they are seeing more of each other because Jenner lives so close to him. In addition, her new single status is reportedly appealing to the rapper, who has had relationships with other high-profile celebrities like Rihanna.

Adding fuel to the fire, Drake recently described his “perfect woman” as someone with her own aspirations and ideals, someone who understands his high-powered work ethic. Certainly, this description fits Jenner to a T, as she is a self-made billionaire who created one of the world’s most popular cosmetics companies. 

How long have Kylie Jenner and Drake known each other?

Jenner and Drake’s history is actually relatively lengthy. They reportedly met in 2013, when Jenner was 16 years old. Drake was even the featured artist who performed at Jenner’s blowout birthday party that year.

They have encountered each other on and off in the years since, although never seemingly in a romantic way. Drake has been known to attend the Kardashian family’s annual Christmas celebration and has even been spotted at many of the same parties that Jenner and her sisters have attended.

Still, it wasn’t until recently when things started to reportedly heat up between the pair.

It would be awkward for Drake to date Kylie Jenner

Kylie Jenner Christmas
Kylie Jenner | Jeff Kravitz/FilmMagic

In spite of their rumored romance, if Jenner and Drake really are dating, it would certainly introduce a lot of awkwardness into the family dynamic.

Drake and Jenner’s brother-in-law, Kanye West, have a long-running feud that boiled over in 2018 when Drake rapped about a woman that many people (including West) assumed was Kim Kardashian. In a recent interview, Drake confirmed the feud and even stated that he has no interest in even communicating with West at this point in time. It seems unlikely that Jenner and Drake would ever be able to have civil family get-togethers with such a bad feud in the mix.

Travis Scott, Jenner’s ex, was also briefly involved in the feud between Drake and West, complicating things even further. While Scott hasn’t really spoken out about any bad blood with Drake, he is known to be close with West.

Then, of course, there is the age difference between Drake and Jenner. Kylie Jenner is 22 and Drake is 33 — a fairly substantial age gap. Although Jenner is known to have a fondness for older men: Her first real romantic relationship was with Tyga, a rapper who is eight years her senior.

Whether or not the dating rumors or true, it will be interesting to see how these two continue their friendship this year.