Drake and Serena Williams dated off and on from 2011 till about 2015 before she met her new man, Reddit co-founder Alexis Ohanian. Looks like their engagement bothered him as he kinda shaded it on his new album, More Life. There's a track there called Nothings Into Somethings where he spits,
"Did I just read that you just got engaged on me? I heard from your friend, you couldn't even tell me or better yet, wait on me"
"Ask about that, you would say it was nothing . But here's another nothing that you made into something."Many think he's referring to Serena because her fiancé's screen name is Kn0thing.