9) Drake

Several high-profile relationships and dating rumors are observed throughout his relationship history. He dated Rihanna and had an on-again-off-again relationship with the singer between 2009 and 2016. He was also rumored to be dating Jennifer Lopez at the beginning of 2017. Then, there was a relationship with model Johanna Leia in 2021.
There are many stories regarding flirtations between Drake and female celebrities; however, he usually avoids publicity surrounding his private life, so he hasn't made a public long-term relationship lately.
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Edited by Priscillah Mueni