Kris Jenner is many things: a mother, an epic momager, an avid martini drinker, and the matriarch of the billion-dollar empire that is the Kardashian family.

With Jenner’s role juggling her kids’ bustling careers, it’s understandable why Jenner is often seen with a stiff olive-topped drink in her hand on “Keeping Up With The Kardashians.”

Ever since her family’s infamous reality series “Keeping Up With The Kardashians” debuted nearly two decades ago, the personal lives of her and her six children have become a pop culture phenomenon. Sex tapes, illicit affairs, pop culture bombshells, divorces, marriages, and many grandchildren later, the lives of the Kardashian-Jenner clan continue to dominate the news cycle.

Without Jenner, none of the immense success the Kardashians have achieved would have been possible — so much so that she even trademarked the phrase ‘momager.’

Because of her place at the center of the madness, Jenner’s romantic relationships have long been scrutinized. After her first marriage to the late Robert Kardashian ended in divorce and her second marriage with Caitlyn Jenner followed suit, the “Kardashians” star found love again with Corey Gamble.

While the pair have been together for nearly a decade, many fans (and her own children) have often criticized the talent manager as being less than transparent about his own life.

Gamble may have taken a gamble of his own by involving himself with someone over two decades his senior — not to mention the head of one of America’s most famous families. We’re breaking down all the strange things about Kris Jenner and Corey Gamble’s relationship.