Hearing from the shadchan or people who know him is important, hearing from him directly is also important- especially how he deals with the aftermath of the divorce now, which will be very relevant to anyone he wants to marry.
I don’t think Lavender is being timid, just wanting to know when is the right time to ask very personal questions without risking a relationship that may not be deep enough yet to handle such big issues. Again, I think a shadchan is a good resource for finding out what the other side is thinking and what he is ready for and whether it is appropriate to ask him directly at this point.
But I do have a feeling that he is really itching to talk about it, but doesn’t know if you are ready.