When Did Drake Date SZA? Full Relationship Timeline Explained As She Once Called It A ‘Childish Fling’

Drake and SZA’s past relationship has once again captured attention, especially as SZA performs at the 2025 Super Bowl Halftime Show and later embarks on a tour with Drake’s rival, Kendrick Lamar. Here’s a closer look at their connection over the years.

2008-2009: A Brief Romance

Drake and SZA reportedly had a brief fling during 2008 or 2009.

This relationship remained mostly private until a decade later when Drake mentioned it in his 2020 song “Mr. Right Now,” stating that he had dated SZA back in 2008. SZA later confirmed the relationship, but corrected the timeline to 2009.

She referred to it as a “childish” fling, explaining it was an innocent, youthful connection.

October 2020: Public Revelation

On October 2, 2020, Drake revealed their past relationship in his song “Mr. Right Now” featuring Metro Boomin and 21 Savage, singing, “Yeah, said she wanna f–k to some SZA, wait / ‘Cause I used to date SZA back in ’08.” Two days later, SZA took to social media to clarify that the fling took place in 2009, not 2008, and explained it was a completely innocent relationship.

December 2022: SZA’s “Mean Girls” Comparison

In December 2022, SZA compared Drake to Regina George from Mean Girls during an interview. She described him as having a “Regina George quality,” referring to his popularity and occasional drama. SZA also reflected on their past interactions, emphasizing that she never felt any awkwardness between them, and she admired his honesty.

2023: Collaborative Tracks

In 2023, Drake and SZA reunited for the first time musically since their fling. They collaborated on two tracks from Drake’s album For All The Dogs: “Slime You Out” and “Rich Baby Daddy.” This marked a significant professional partnership after years of their personal connection.

SZA downplayed the intensity of their relationship in an interview with Rolling Stone, describing it as “childish” and “not hot and heavy.” She mentioned that both of them were quite young at the time and there was no deep emotional connection.

In a separate interview, SZA expressed concerns about Drake potentially “sabotaging” her music by using a first draft of her feature for the track “Slime You Out” instead of her revised version. Despite this, she acknowledged that their working relationship has always been positive, and she respects him.

2024: SZA Gets Involved in the Drake-Kendrick Lamar Feud

In April 2024, SZA found herself unexpectedly drawn into the ongoing feud between Drake and Kendrick Lamar. A leaked demo of Drake’s diss track, “Push Ups,” featured a line about SZA being more deserving of a spot in rap’s “Big 3” than Lamar. SZA humorously reacted to the situation on Instagram, expressing her confusion about being caught in the middle of the beef.

Months after the feud between Drake and Kendrick Lamar escalated, SZA collaborated with Lamar again, featuring on two tracks from his album GNX—”Gloria” and “Luther.” This collaboration marked their first since the public dispute between the two men.

In December 2024, it was announced that SZA would be the opening act for Kendrick Lamar’s Grand National Tour, which kicks off in April 2025. This further solidified her partnership with Lamar amid her past connection with Drake.

January 2025: SZA Joins Kendrick Lamar at Super Bowl

In January 2025, Kendrick Lamar announced that SZA would perform alongside him at the Apple Music Super Bowl Halftime Show, which took place in February 2025, continuing their ongoing professional collaboration.

During a promotional interview on Hot Ones Versus in January 2025, SZA was asked whether Drake was a good kisser, to which she avoided answering, stating, “We were children” at the time. Her response amused her fellow guests, Issa Rae and Keke Palmer, who pushed her for an answer, but SZA maintained her playful stance.

Despite their past romance, SZA and Drake seem to maintain a cordial relationship. SZA has emphasized that she holds no ill will toward Drake, and she appreciates the positive way he has spoken about her over the years.

Their interactions have remained friendly and professional, even as they continue to work with other artists like Kendrick Lamar.