Kourtney Kardashian & Sofia Richie
Talk about a modern family. Kourtney and Scott have always had a rather nontraditional relationship, but since he's started dating Sofia Richie it's gotten even more, um, interesting. Not technically in a bad way. In order to spend time as a family, Kourtney and Scott often take vacations together with their children, and she doesn't mind hanging out with his girlfriend, who is 16 years his junior. Although Scott did recently reveal on KUWTK that he was afraid Sofia felt uncomfortable, it seems everyone is friendly enough.
[Photo via @letthelordbewithyou]