It speaks to your maturity and character that you want to start your marriage with a clean slate. I would hope that your boyfriend understand that there’s a difference between lying and keeping personal things private. Lies are meant to manipulate and deceive. Privacy is about self-protection and preserving some personal boundaries. I think the stories you’ve shared fall into the latter category.
Let’s start with the easy one first: You ran up debt when you wee younger. You have been doing the honorable thing and are paying it off before you marry. You aren’t asking him to be burdened by it. It seems to me that this is your own business. If you choose to share it, I would hope that your boyfriend would see that not only did you learn your lesson about debt but that you have learned how to handle money so it won’t be a problem between you.
The miscarriage does require a conversation. You didn’t lie. You don’t have children. But you didn’t tell the whole truth either and medical history could affect things in the future. It’s understandable that in the early stages of your relationship you wanted to keep such a personal thing private. As your intimacy with your boyfriend has increased, the boundaries between what is personal and what affects both of you has changed. I imagine you and your boyfriend will want children someday. Your doctor will want to know about prior pregnancies in order to give you the best care. In general, family members shouldn’t know things that your husband doesn’t.
You are 30. I imagine both of you have done things in the past that you wish you hadn’t. People who have lived life and had experiences generally also have some regrets. Regardless, all of our experiences shape us into who we are as adults. We don’t get to pick and choose. I hope that you and your boyfriend will be able to talk about your histories with a focus on who you’ve become and your hopes for the future.
I worry about your level of worry about such a conversation. If your boyfriend is so judgmental that he can’t be understanding and sympathetic when you talk about such issues, maybe you should rethink marrying him. Life is far too complicated to hold it against someone for being private about private matters.
I wish you well.