The 34-year-old socialite was happy to support her younger sibling when she announced she was going to wed the basketball star - who she filed for divorce from just 72 days after they tied the knot - but refused to lie and says she didn't approve of their union.
"I said how I felt before they got married. I love my sister and will support her no matter what but I'll also be a good sister and say this is how I feel, I'll come to your wedding and do what you want me to do but I can't lie and say this is perfect if I feel it in my heart, I just didn't agree with it."
Speaking on 'The Tonight Show with Jay Leno', she revealed: "When I met Kris for the first time I'd just landed in New York and it was late at night, around 10. He was in Kourtney and Kim's suite so I went in to say hi because Kim had been like, 'Oh I want to introduce you to my friend,' because they had just started dating.
"And one of the first things that came out of his mouth within five minutes was, 'So how much are you getting paid to fake your marriage? How long can you keep this up for?' I was like, 'Dude. I don't know if you're trying to make me laugh or not,' but it rubbed me up the wrong way.
"So since then I had a very defensive wall up [around Kris]. I'm a very good judge of character - if I do say so myself - and he just rubbed me up the wrong way."