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

- By Bossip Staff
1 of 15

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.

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

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

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?

    Continue Slideshow

    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?

    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

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

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

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

    More Stories From Bossip


    Bossip Comment Policy
    Please read our Comment Policy before commenting.