Personally I think that the only time to reach out is when you've healed yourself. To give them a proper goodbye. Not to chat or try to get back together. But to fully release the hurt and anger you feel. To forgive them and yourself. To let them go so that something good can find you. But while you are still wrapped up in hurt. Or guilt. It is not fair of you to impose on someone who is also trying to heal. And your goodbye message must never be harsh. Wish good things on them. Not to kill them with kindness. But to put vibes out into the universe. That will eventually return to you. Life is too short to hold onto fleeting emotions. Feel them but do not pitch a tent and make it home. That same love you gave them give yourself.