Ray J
This relationship might actually be the most highly noted one, but Kris Humphries deserved the top spot on the list. Kim K. probably grew her empire from the infamous sex tape which was accidentally “leaked” online, for millions of people to see.
The record producer and Kim K. dated from 2005 to 2007, and were reportedly together several times following this period. Whether you remember the relationship or the tape, it is what many people believe launched Kim K. (and her family), into stardom. Honestly, this should have been an indication of what the public could expect to follow since scandal and attention seem to continuously follow Kim Kardashian.
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