Love Conquers All
Even though Xander seemed very proud of having Anna in the palm of his hands while continuing to flirt with other women, he actually did not really feel that great about it.
Not letting Anna go meant Xander would not be able to move on either. Thus, Randall was really afraid that one day, Xander would go crazy and drag Anna down with him.
As for Yaacob, he was obviously in love with Nancy, but he chose not to admit it. In other words, he would not allow himself to get into a relationship where he did not have absolute control. He was the epitome of once bitten, twice shy.
Randall wanted to tell Yaacob that Ain and Nancy were completely different women. After all, Ain was a psychopathic woman
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