When should you break the "no contact" rule with your ex?

I’m thinking of doing “no contact” with my ex that just broke up with me a few days ago. I want to break the habit of talking every single day for the past 5.5 years. We’ve been good friends for 2 years before we dated, he even helped me through heartache once. Since the break up, he’s been contacting me trying to be friends…but I can still feel the pain between us when we skype and talk…he isn’t happy and neither am I.

I told him about “no contact” last night and he got really upset because he thinks I’d disappear forever for good. He then asked if he could please just try it out for a week and see…and if he could call me when he needs me because I’ve been his confidant over the years and he talks to no one else about his feelings. I didn’t know what to say because I don’t want to regret making him think I wasn’t there for him.

He asked how long will I not contact him. I said I didn’t know…honestly…do I contact him when I don’t love him anymore? When there’s no more pain? What do I do? What if I love him after a year and still don’t feel ready to contact him then I’d lose him as a friend.

I did tell him that no matter how many months goes by, when I do contact him and he doesn’t want to be friends then he never truly wanted to be friends but wanted me as a comfort pillow. I feel that even if we keep in touch right now…there is no guarantee we won’t drift.

Final questions
How do I know I’m ready to contact him?
When do you know you stopped loving them?
What if I regret no contact and things get worse for me?