Drake used to have some major beef with one of Kylie Jenner‘s ex-boyfriends.

Multiple sources have revealed that the beauty mogul, 22, and “Hotline Bling” rapper, 33, have been spending time together “romantically” following her split from Travis Scott. While there’s no known grievance between Drake and Jenner’s most recent ex, the “God’s Plan” singer once had a very public feud with fellow rapper Tyga — who dated the Keeping Up with the Kardashians star from 2015 through 2017.

At one point, Jenner seemed to be caught in the middle of it.

The quarrel between Tyga, 29, and Drake escalated in 2014 when Tyga claimed to Vibe magazine that his friendship with Drake had been forced by their then-mutual music label, YMCMB.

“I don’t like Drake as a person. He’s just fake to me,” the “Taste” singer said. “We were forced together and it was kinda like we were forcing relationships together.”

DAVID M. BENETT/WIREIMAGE; JEFF KRAVITZ/FILMMAGIC; STEFANIE KEENAN/GETTY

After those remarks, the pair engaged in a series of public, back-and-forth shade through their music and social media. Drake followed up Tyga’s Vibe interview by liking all of Blac Chyna’s Instagram posts, according to BBC. She and Tyga had recently split at the time and is the mother to his now 7-year-old son, King Cairo.

Tyga responded by calling out Drake in his “Make It Work” track in October 2014, with lyrics that seem to say Drake had never been his “homie” and also called the “Money in the Grave” singer “corny.” Meanwhile, rumors had been circulating that Tyga and Jenner had been dating, even though she was still a minor at the time.

Drake’s next move was to share a photo of Jenner in his studio on his Instagram in November 2014, captioning it, “@kyliejenner in the cut.” In February 2015, he released a surprised album with a track titled “6 PM in New York” that directly called out Tyga and his rumored relationship with Kylie.

The lyrics go: “I heard a little little homie talking reckless in VIBE/That’s quite a platform you chose, you should’ve kept it inside/Oh, you tried/It’s so childish calling my name on the world stage/You need to act your age and not your girl’s age.”

Following the song’s release, Tyga came forward to deny that he was in a relationship with Jenner, who was still 17 at the time, while appearing on The Breakfast Club, according to Vibe. The couple made their relationship official in August 2015, after she had turned 18, before calling it quits in 2017.

Jenner went on to date Scott, 28, in April 2017. They welcomed 1-year-old daughter Stormi Webster in 2018, but PEOPLE confirmed that the pair called it quits last month.

Travis Scott, Stormi Webster, Kylie Jenner. TOMMASO BODDI/GETTY IMAGES

On Wednesday, multiple sources revealed to PEOPLE that Drake and Jenner were hanging out amid her breakup.

“He and Kylie have been spending time together recently,” a source told PEOPLE exclusively. “They’ve been friends for a long time and Drake is very close to the family.”

Another friend added that Kylie and the rapper have been hanging out “romantically” since she and Scott called it quits in October.

ETHAN MILLER/GETTY IMAGES, BRYAN STEFFY/WIREIMAGE

However, while some close to the reality star and the “In My Feelings” rapper see a potential romance blossoming, another insider insisted the duo are “just friends.” A source close to the makeup mogul also denied the pair is dating.

News of their recent hangouts comes after Jenner attended Drake’s 33rd birthday bash last week at Goya Studios in Los Angeles. She was also spotted at Drake’s Halloween party in West Hollywood on Thursday, a source tells PEOPLE, adding that she stayed “super late.”

The Kylie Cosmetics founder and her big sister Kendall Jenner also attended Drake’s New Year’s Eve party at L.A. hotspot Delilah in January.

Drake has been single in recent months, and like Jenner, is also a parent. He shares 2-year-old son Adonis with artist and former adult film star Sophie Brussaux.