I find OCD to be so tricky because when I think to say something I immediately start thinking about the possibility that whatever I say could have unintended meanings that could cause more harm than good. And it seems the only way to mitigate that effect is with more words. (This is an illusion, I think.) Having said that, I feel the need to reply here partly because I see no one else did. (Maybe you got some private messages though.) To start, and I hate to bring this up if it's something you've been able to get some distance on, but you mentioned that your earlier obsessions with going to hell were helped by logical argumentation. I guess my question to you is whether logical arguments could help in your current uncertainty intolerance when it comes to the guarantee of intimacy with a woman. As you've said, you can have no real certainty when it comes to this, just like I can have no certainty that my words won't strike you in unintended, perhaps even harmful ways. Would it help to know that there is no such certainty to be had? The flip side of that despair is that, when it comes to others, we can at least be certain of some level of unpredictability. Maybe that is not comforting, but it may help you start to recognize patterns in communication. At least I can tell you that I've "scared off" women plenty of times in my life, probably via the same or similar routes you describe here, and the amazing thing is that the world is just full of them. So you will have plenty of opportunity to perfect your approach to the opposite sex. And you're young still. Try with someone your own age. You might come across people who are fickle or flighty, and you'll have to learn how to pace your texts with them. Don't give everything upfront. Keep them looking forward to your replies, not always playing defense. And of course I know nothing about your relationship with the 31 year old, but I will say that's a very large age gap to have when you're that young (21) and for what I assume is your first serious relationship. I hope this helps somewhat. I know it's not easy, but take what refuge you can in the fact that your struggles have been had before, by others. You can survive this, and though you might not crack the code (codes can't always be cracked), you might be able to come to a place of relative tolerance, even peace, around what today presents itself to you in the form of obsession. You've overcome a lot already, so you have it in you for sure.