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-faust-and-nikko Mimi and Nikko - They made an adult tape together and it only made them look more awkward. Our eyes still hurt.
KhloeFrench Khloe Kardashian and French Montana - What's going on with this?
woody-allen-and-wife Woody Allen and Soon-Yi Previn - He definitely married his step-daughter. Nobody finds anything wrong with this?
kim-kardashian-kris-humphries-divorce-e1320155613357 Kris Humphries and Kim Kardashian - Nobody bought their relationship and it ended in a couple of weeks.
scott-kim Scott Storch and Lil Kim - Drugs. Moving on.
50-cent-and-chelsea-handler-in-bed1 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.
katietom 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-rihanna-hate Drake and Rihanna - Drake. She never liked you. And it was sad to watch.

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