Is it a good idea to meet someone from my past given that I have conflicting emotions about him? I am going through a bad phase after a recent break-up and am not sure what I want or what I’m looking for from a relationship anymore. This person and I dated for a while and ended it because we were not sure about the future. I am conflicted because a part of me feels as if I will just get into a relationship with someone to stop feeling so vulnerable. I know the smart thing is to wait, but I am also insecure and feel as if I should be with someone just to get out of this rut. What should I do? Should I just meet him and chat?
You are self-aware enough to recognise that what you choose to do will depend upon your state of mind more than whether you want to be with someone. If you are vulnerable, that is normal given that you are getting over the demise of a relationship. It’s okay to meet anyone, chat, and talk about how you’re feeling. The idea of getting into a new relationship to stop feeling insecure or to feel less vulnerable doesn’t work because you aren’t addressing the underlying causes of why you feel this way. It makes more sense to spend time trying to understand yourself. Think of it as a period of reflection when you can focus on why you want to be with someone, what you expect from any relationship, and why you feel unable to stay single until you figure these things out. There’s nothing wrong with meeting your ex and getting back with him, but you are possibly causing yourself more harm than good.

I am becoming very close with my best friend’s ex-boyfriend and don’t know if this will damage our friendship. Should I tell her about it?
If this is a friend you value and a friendship you want to retain, you should be honest about everything.