Code Violations: Drake’s Pettiest, Messiest Relationship Moments

- By Bossip Staff
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2016 MTV Video Music Awards as seen on MTV.

Drake’s Pettiest Relationship Moments

Drake is one of the most notoriously petty men in the history of celebrity. He has no problem trying to take someone’s woman, put someone on blast or try his luck with side chicks. And he’s happy to do it all in public. And now that his relationship with…

Drake Rihanna Kiss Miami Instagram

Appears to be over, it’s time for Drake to get back out in the world and be his natural, petty self. Before he does that, let’s take a look at his most petty, messy moments.

Chris Brown Drake Rihanna

That time he sent Chris Brown a message at the club about smashing Rihanna, leading to that fracas and light skinned feelings getting hurt.


Drake has confessed his love to Nicki a million times and did so while she was still with Safaree.


He also did this with her while she was with Safaree, too.

wENN AP Images Serena Williams Drake Rihanna

He dissed Common and threw in some subs about laying in bed with Serena Williams in the process.

Drake Crystal and India Love Westbrooks

Drizzy is chopping down India Love…but her sister said she hit it first. Yikes.


Lil Wayne just revealed that Drake smashed his girl while Wayne was in jail. Dirty.

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He took Amber Rose out on a date as soon as she and Kanye West broke up…no shame.


Drake sent shots at Tyga, telling him to act his age and not his girl’s age, putting Tyga and his statutory bae on blast.

Drake Kylie Jenner

Also, while Drake was fighting with Tyga, he posted a pic of himself with Kylie.

Tyga Nicki Minaj Drake Kylie Jenner Blac Chyna

Drake also posted a flirty message to Blac Chyna during the whole fiasco too.

Drake allegedly broke up with Dollicia over the fact she didn’t like his colored contacts. Petty on petty.

Christina MIlian Karrueche Hooray Henrys all white West Hollywood Drake The Game

Chris Brown accused Drake of trying to get at Karrueche while they were dating.

Drake All Black bomber jacket and velvet track pants Serena Williams wannabe/lookalike The Nice Guy West Hollywood

The rumor is that Drizzy had this chick with him while he was dating Serena and had a rough time juggling the side chicks and his main bae.


Drake said he loved Rihanna for years…which means his other little girls were just there for show.

He took Nicole Scherzinger out immediately after she broke up with her longtime Nascar bae.

Drake Joe Budden

Budden claims Tahiry and Drake got together…maybe that’s why Budden is so mad.


Now take a look at some of the other times Drake’s been creeping around with women.

Drake gives Christina Milian a friendly kiss goodnight, while her fiancé Jas Prince stands close by. The trio was joined by Rihanna for a fun night at Supper Club in Hollywood. Drake, who was flanked by big beefy bodyguards, arrived at the club around midnight and left around 2 AM. Rihanna arrived at Supper Club shortly after Drake and stayed until closing time.

Karrueche Tran enjoyed a date night at the LA Clippers vs. OKC Thunder game in LA. She looked hot in an unbuttoned white shirt over a crop top and very short shorts. Chris’ other ex-Rihanna also happened to be in attendance with her renewed interest Drake!


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