Keep the shadchan involved all the way through. Even if you feel comfortable enough to stop ‘reporting’ to the shadchan. You never know when you might need their service again.
In general, you should not be using the shadchan as a go-between. Most conversations should take place between the two of you – without a third-party. If this was to become a marriage, you will have to have uncomfortable conversations without the shadchan’s assistance. Begin to experience that at this early stage.
Additionally, oftentimes, the shadchan may add their own layers to what is asked or said. It is best to hear it directly from the person – in their own words, with their nonverbals and body language. If you are trying to work out when to meet again, it is best to do that directly. You’ll begin to get a sense of how you can work things out together. (As an example, if someone replies to the shadchan, ‘how could they not be available?’, most likely, the shadchan will not relay the message in those words and tone. But that would be important for the dater to know how they responded, not only a final answer.)
But, there may be some circumstances that you might need their assistance.
A shadchan can help you navigate tricky situations. They can pass along some concerns to the other person, in a sensitive, delicate way. For example, your hesitation might be that you are concerned about what it might be like to join their family, with all their familial issues. Yet you are having a hard time asking the relevant questions without dredging up uncomfortable feelings for them. The shadchan might speak with them, “As you might expect, anyone who is joining your family is concerned about your family’s situation. Did you speak about that yet?”
You might also want the shadchan to help you know if she is ready for a proposal.