What Are We Doing: The Most Awkward Celebrity Couples Of All Time

- By Bossip Staff Categories: Coupled Up, For Your Viewing Pleasure, Knocked Up

Mariah Carey and Nick Cannon share a kiss in Paris [USA ONLY]

The Most Awkward Celebrity Couples Of All Time

Some celebrity couples make a ton of sense. Others are just awkward from jump. These are some of the most random, awkward couples of all time.

Janet Jackson Jermaine Dupri

Jermaine Dupri and Janet Jackson – This was awkward from the jump and nobody believed it was possible.

Mariah Carey and Nick Cannon share a kiss in Paris [USA ONLY]

Nick Cannon and Mariah Carey – You ever see them kiss? Yikes.

In White Folks News: Ex- Hubby Billy Bob Thorton Is Reportedly Making A New Movie About Angelina "Wild Woman" Jolie

Angelina Jolie and Billy Bob Thorton – They looked really weird together.


Mimi and Nikko – They made an adult tape together and it only made them look more awkward. Our eyes still hurt.


Khloe Kardashian and French Montana – What’s going on with this?


Woody Allen and Soon-Yi Previn – He definitely married his step-daughter. Nobody finds anything wrong with this?


Kris Humphries and Kim Kardashian – Nobody bought their relationship and it ended in a couple of weeks.


Scott Storch and Lil Kim – Drugs. Moving on.


50 Cent and Chelsea Handler – What was going on in 50’s head though?

Rumored couple Christina Milian and Lil Wayne wrap up a low-key dinner date at Mastro’s Steakhouse in Beverly Hills.

Lil Wayne and Christina Milian – Milian’s baby daddy is the Dream who is also Nivea’s baby daddy so this is incredibly weird.


Tom Cruise and Katie Holmes Nobody believed this beard-y weirdness

2006 NBA Rookie Sophomore Practice

Bow Wow and Ciara – She was like a foot taller than him and…ugh.

*EXCLUSIVE* Jennifer Lopez and Casper Smart hand-in-hand on set of A.I.

J. Lo and Casper Smart – “You could do better…” – Drake


Drake and Rihanna – Drake. She never liked you. And it was sad to watch.


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