Causality was the big question for Dylan, for lots of people, and the angel marriages were just the pop culture version of the question. It was especially common among religious types which, unfortunately, there were a lot more of since the appearance of the angels.
There was a part of Dylan that actually wanted to do his next book on them, but he wasn’t sure how he felt about the comparisons to his own marriage that would inevitably bring. He had a reputation, not undeserved, for being prickly, and it could manifest at inopportune times.
He didn’t necessarily have a problem with people getting married because the angels said they would. His marriage, while very definitely not an “angel marriage” was also undeniably a result of the messages that he and his wife had received. He wasn’t against a little light hypocrisy now and again, but trying to act like that wasn’t the case would be a step or five too far.
What bothered him was the notion that the angels wanted these people to get married, and that they were destined by god to be together. The notion that they were special, that their union was made, quiet literally, in the heavens. This was an entirely different animal, to Dylan’s mind, than meeting someone because of the message and then it happening to work out, which was the case with Dylan and Molly.
For one thing, Dylan had complied thousands of messages from hundreds of people, and there was nothing in that entire mass of information that indicated that the angels cared about people. Some of the information they send couldn’t be acted on, and much of it was things that people would probably be better off not knowing. Dylan wasn’t convinced that there was an intelligence at all behind them, necessarily, and certainly not one that cared about people.
But it was the notion that they were special that he found particularly grating. The angels sent messages all the time, to everyone. They sent messages about significant life events and things that didn’t matter at all. The truth was that if you were in a position where you could receive messages from the angels and you were going to get married, they would almost certainly tell you about it. It was, in fact, the exact opposite of special.
Not surprisingly, the angel marriages didn’t work out all that often. They worked better with people who had a solid religious upbringing prior to the angels coming and were willing to work on it. But for people whose conversion to religion, often their own cobbled together versions of religions that bore about as much resemblance to the real things as a cubist painting to the subject, they often did not.