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To make matters even more complicated, he used to date her sister, Crystal Westbrooks.
In late October, he appeared to have moved on again, and was linked to pop princess Taylor Swift after the pair were seen flirting at his birthday bash and rarely leaving each other's sides.
However, by October, Drake had already reportedly moved on to reality star and Instagram model India Love - after his and Rihanna's gruelling work schedules proved too much for an exclusive relationship.
Half Jamaican and half Irish Instagram model, Malaika is Drake’s new bae, apparently.
The 31-year-old was pictured walking around Toronto with the 22-year-old and according to sources things are getting serious, so serious that Malaika has apparently even met the "Duppy Freestyle" rapper's mum.
Rihanna, 28, and Drake had only just called time on their romance after he publicly confessed his love for her at the MTV Music Awards in August.
Jennifer had worked with Rihanna on the animated film Home in 2015 and in the past have gushed about their mutual admiration for one another.
Drake, the 31-year-old sentimental Romeo of rap, is apparently dating an 18-year-old model now, E! Bella Harris was out with him for two nights in Washington, D. The two's proper public-ish date was Monday: Drake closed down D. Dating rumors first started last month, when Harris shared a photo of her and Drake together.