I don't doubt that his current feelings make his judgement of you more extreme than in the past, but if you are saying that this happened before (even to a lesser extent) that's something that he should recognize. It's not fair/healthy to be in a relationship with someone who sees themselves as better than you. It could be how he was raised, it could be for any number of reasons, what's important though is whether or not he's willing to change the behaviour and if not, is this something you want to accept in your relationship. You say that it's more upsetting that he treats your family in this way than that he treats you this way -why? I know we are always protective of our families, but we need to be protective of ourselves as well. And another thought, if this is a behaviour he's always going to exhibit, how will it impact your son. If he sees/hears your bf talking down to you (even if you think it's being kept separate from him, as he gets older, kids pick up on things) he may see that as the way he is supposed to treat women.

The how/why question. It's partly that we truly do want the answer, but another big part is that it's a cry of distress, it's a step to processing what happened. Once we can wrap our hands around the fact that it did happen and we begin to accept that as a fact the question becomes less frequent. Your explanation of what you were thinking didn't make it worse, a lie would have. See if you lie, and he finds out otherwise, he will have two new hurts
1) The fact that you lied
2) After accepting one thing, he will have to go through the process of accepting the new thing
Even if it sucks, and it hurts and it makes you sick to think about, the truth is the better answer. It restores his trust and helps your conscious. You can't change what happened, what you can do is figure out why you let it happen (which I know you are working on) to that it doesn't reoccur. Look at how you view sex, what your justifications were.

I still don't see borrowing money from you as a sacrifice. Like TheByz said, he made those choices, and yes he did it for you, but that's a relationship. If that's the view he's going to take than everything is a sacrifice. Last night for dinner I had chicken, potatoes and salad because I had dinner at my bf's and that's what was on the menu. So did I sacrifice pizza, chips and ice cream? I guess so, but is that something I can/should hold over his head? Heck no, I was happy to have dinner with him. Do you understand what I'm getting at? Relationships are about compromise, but we make them because the person we are with are worth it. Did you force him to move with you? No. Were you happy to have him there? Yes. Did you plan for him to be jobless (in an awful economy where unemployment is high everywhere btw)? Of course not. He needs to own his part of this decision.

I agree with your counselor that he's projecting his problems on you. Again, this might be where I'm similar to him in mindset. Growing up, I've always been a perfectionist, I've set unreasonably high standards for myself (no one else, just me). This year I was diagnosed with GAD. I've always known that I'm a 'worrier', I figured it would go away if I could just do better. Officially being diagnosed threw my world on a tilt. Now I could never be "perfect", something is wrong with me. I've had so many conflicting emotions about how GAD has ruined my plans for life. My counselor mentioned that I see it as a life sentence, I do. I'll never be able to do this, this way because I'm broken. It's just something that I cannot allow myself to accept, and I feel your bf may have a similar view.

I don't think you are being oversensitive. He's putting 3 years worth of relationship on your shoulders and saying "thanks for all these problems". You said that you want the challenge of saving the relationship. I wonder about your motivations to this. What is your view of this not working out? Do you see it as personal failure to overcome this. Do you need his presence and forgiveness to forgive yourself?

I understand the emails coming across more negatively than other forms of communication. Simply because that's what happened with us. Everyone needs to find what works for them. But I agree that he may be manipulating your "need him emotionally"