Ray and Kyrie are both like ex-girlfriends.
Ray was the girlfriend you spent several years with, had some great times with, but the relationship got a little stale, and she decided to leave before you were ready for the breakup. Looking back on it now, you're still not happy with the way it ended, but no hard feelings, you can see where they were coming from. You moved on, and you're glad to hear they're doing good. Could even catch up over coffee sometime.
Kyrie was the girlfriend who was super hot but had a ton of flaws you overlooked because of the hotness and your desire to be in a relationship. In the beginning of the relationship she seemed committed, but after a very brief honeymoon period, the relationship was just a disaster filled with jealousy, lying, cheating, empty promises, manipulation, emotional abuse, etc. She ends up leaving you for the guy that she always claimed was "just a friend" and yet still talks trash about you like it was your fault things didn't work it and taking no responsibility for the failed relationship. You want nothing to do with her, would never take her back, but can't help but smile when you hear the guy she cheated on you with cheated on her, or you hear she got arrested for a DUI, or that she got fired for throwing a tantrum at work, etc. And if you do happen to hear she's doing good, you first thought is "just a matter of time before she ruins this too."
That's kinda how I view Ray and Kyrie situations.