I've discussed this before, and people seemed interested in the plan, so here's an update.
My future husband and I had our second wedding-related meeting with a Priest yesterday. The first meeting was with the curate, who will officiate. This meeting was with the rector, who supervises the curate.
We discussed the wedding date and some light stuff about how we met and my future husband's profession and his Catholic conversion process. The people of my parish have known me since I was 12, so there wasn't much about me individually for the rector to ask. He did keep asking whether we had any questions or issues we wanted to raise this early in the process.
I didn't want to bring up the chuppah and glass-breaking at this early meeting, because I knew the Priest didn't want to discuss liturgical details this early in the process. We actually joked about that in the e-mails setting up the meeting. But my future husband knows less about canonical issues v. liturgical issues, and he brought it up, which was, of course, fine.
Knowing we're both "from Jewish backgrounds," the Priest said he actually expected we'd want to break a glass during our ceremony, and he looked forward to incorporating that tradition. He knew less about the chuppah tradition, and it raises issues of people still being able to reach the altar rail, but we'll likely have a chuppah, too.