Justin Bieber and Kourtney Kardashian
This friendship made headlines the second that these two were spotted out. Even though they are both A-List celebrities, their age gap made this a pretty bizarre friendship. Kourtney Kardashian is 40 years old while Justin Bieber is 25. They started hanging out when the singer was around 21 or 22.
Rashida Jones and Natalie Portman
Even though Natalie Portman usually takes on more serious roles, she still has an awesome comedic side to her. That's what makes her friendship with Rashida Jones so pure! They've also done some skits with FunnyOrDie where their friendship chemistry is on point. There should be more skits with these besties...