I don't think "none of your business" translates well into Catholic

You don't want a Catholic wedding, or a wedding at all. Your boyfriend (not, not fiancee!) is currently indicating he doesn't care if you two have a Catholic wedding. Why are you considering preemptively preparing for a wedding that neither of you has a desire to go through with right now? At the very least, this can wait until he actually proposes to you.

First, I think you should get a second opinion (if possible) or ask to speak to someone who's been through the annulment process in your diocese before deciding whether to proceed. How difficult the process is can depend on the diocese. Second, I'm Catholic, and, look, one of the biggest arguments in favor of no-fault (civil) divorce is that it dramatically protects abused women. When women who are victims of abuse can seek a divorce without having to assign fault or go through the fault process, they are more likely to seek the divorce and more likely to get it safely because it doesn't as directly affront a man who's already abusive and controlling. I'm well-aware that there are many divorced-but-not-annulled women in the Catholic Church who can't face an annulment both because it's cruel to force someone to go through that a second time (having gotten up the courage to go through it once!) and because you can't (as far as I'm aware) get an annulment without contacting the ex-spouse as well. Which is to say, as a Catholic, I don't give a rat's ass if someone is divorced. If you are divorced and did not seek an annulment, I assume there is a good reason, and I further assume that if you (or your spouse) are serious enough about your faith to be attending church after going through a divorce (given how rude people can be about the fact that you're divorced), that your reasons are between you and God.

Just to clarify, an annulment doesn't actually mean the marriage "never happened" in the sense of a memory eraser ray; it means it wasn't valid at its formation, so it didn't exist, in the way an invalid contract wasn't actually a contract. Also, annulments don't render children illegitimate, which is like not even a thing anymore, since just about everything to do with "legitimacy" of children is now a civil matter (inheritance rights, health care rights), and in most places in the U.S. you're on the hook for supporting your children no matter what the status of your relationship with their other parent is. (I can't think of a darn thing that "legitimacy" would matter for in the U.S. Catholic Church anyway, and a quick glance at canon law didn't turn anything up.) Even in really conservative dioceses and even with older priests, it's pretty unusual to hear the language of "legitimacy" used w/r/t children (including those born of adultery), and I've certainly never heard it used w/r/t an annulled marriage. Canon 1137 is the specific canon law citation that says children of putative (apparently valid at the time, but legally invalid for some reason) marriages are legitimate. Illegitimacy used to be a (potential) bar to priesthood (that was routinely given dispensation), but the 1983 code removed this. I was going to joke that it might still matter if you were attempting to inherit the throne of the UK, but of course A CATHOLIC CAN'T because of that whole thing in the first place.

He already told you that he doesn't want you to worry about it if it's going to be this painful. Moreover, I'm worried that it would be easy to hold it against him in retrospect. So I would tell him how much it's sucking, and why, and get his buy-in on backing out.

Why are you torturing yourself over something that you don't want, that is not consistent with your religious views, that offends you, and is of unclear value? You don't want traditional Catholic values imposed upon you. Don't pay the church actual money for the privilege of doing just that!

That's a bridge we'd cross when we get there though. Honestly, both of you should be aware of that bridge and decide how you're going to cross it now. Talk it out, so that there are no surprises later. You're clearly uncomfortable with a Catholic wedding and marriage and he's clearly looking forward to it, despite him saying it's not a big deal. His friends are clearly expecting a Catholic wedding. He almost surely would like one, seeing as he's more religious than you. Ya'll really need to work this out before getting engaged. As to the annulment proceedings, it sounds like you'll hate and resent it. That's not a good way to start off a marriage.

(Third, I have a really good story about an annulment after one of the spouses was struck by lightning, if you want to memail me.)

I would wonder if your bf is going to remain as enamored of Catholicism once he is a bit more distant from the influence of those particular friends. If he is considerably more devout than you are and continues to become more so, this might be a problem. The present efforts by the church, for example to oppose employer provided plans that include birth control, is very out of tune with the thinking of most Catholics. This is very patriarchal and regressive but the piety and power appeals to some men. Just make sure your guy is not turned on by the certainty of all that pontification because it tends to disempower women and you might not like such an unequal relationship after a while. If you have had run-ins with his friends already about this, let it at least give you pause and have a good long discussion with your bf about how much loss of bodily autonomy and judgment you actually believe is right. I went through this as a young woman and the first application ended with the official telling me there was nothing to be done but "pray for a happy death." It struck me as extremely cynical and unfeeling at the time. In the neighboring state, where my fiance lived and his family had some influence, the application was routed by the parish to the bishop's official who handles such canonical matters. He explained that because my first husband had not been baptized (and I had, although not as a Catholic) this was a case of an unequal marriage unrecognized by the church. This was a long time ago, so things might have changed. At least there are certain reasons why a marriage in the Church can be annulled. It's not just a matter of the interviewer assessing the quality of the marriage or something but the need to find a ruling or canon law which justifies the annulment. LIke most things, it probably still matters how far up the chain of command you can go. And like most things, people tend to change over time--if you have found yourself less fond of religion even though you go to Church with him, and he is very gung-ho, that might be a bit of a caution flag because the Catholic Church shows little or no sign of relaxing their views in these matters. Please do take seriously your reaction to the probing questioning of this process. If it is repugnant to you now, you might not really be able to embrace this religious requirement being imposed. Have a serious and full discussion with your bf. Whatever you do, I wish you well and hope you can find a way for both of you to develop in this happy relationship which doesn't at the same time violate your sense of self and of propriety.

My parents were married in the Catholic church, divorced, and met other people who also had been married in the church and subsequently divorced. So, three annulments would have been required in order for my parents to marry my stepparents. They got part-way into the process and were all "hell no," especially because it would have made me and my step-sisters "bastards." My mom and stepdad got married in a Protestant church but knew a priest who was willing to unofficially co-officiate with the pastor. My dad and stepmom got married in a restaurant by a judge but a priest did a reading. My point is that it's not necessarily a binary thing - Catholic involvement or no Catholic involvement. If you're not comfortable with the annulment, but you or your boyfriend want some religious aspect of it, talk to some more liberal priests. It won't be official in the eyes of the Church, but it doesn't seem like that's a priority for either of you.