Should I reconnect with cheating ex?

My ex-boyfriend and I broke up around five years ago because I caught him cheating. He has moved on and I have also been with other people since then, but I think about him a lot and second-guess myself by wondering if I should have been more forgiving. He was great with me, and we were genuinely in love, which is something I haven’t experienced with anyone. I know this hold he has over me is irrational, but I sometimes ask myself if I should reach out and try rekindling this relationship. We are both older and he must have changed. Is this a good idea?
You moved on from a relationship because of a betrayal of trust. You may have been in love, but it was an unequal relationship because your ex-boyfriend clearly didn’t value you as much as you did him. Yes, you are both older and it’s possible that he may have changed, but being older should also bring a renewed sense of self-worth. You owe it to yourself to make choices that lead you to a better, happier place. If you don’t know anything about how he has changed since you were last together, you can try reaching out and initiating a conversation. As long as you make a decision with your eyes open, and by acknowledging the facts, you should be able to navigate this. It’s also possible that he simply isn’t interested, which is something you should be prepared for too.

I have a crush on my boss who has just quit the organisation. Is it okay for me to finally ask him out?
You are both adults, so asking him out is okay as long as you think about power structures and what any possible relationship may be like, given your history at this company. There’s nothing wrong with asking him out for a cup of coffee and taking things one step at a time, provided you accept that he may also turn you down because he was once your boss.