What Would You Say?

This week I am in Chicago at our denomination’s Midwinter Conference. My roommate is a close friend from seminary and the Worship Director at Cascade Covenant Church in North Bend, Washington.

Last night we went to dinner and as we walked into the restaurant we saw several people we knew that were also in Chicago for the conference. We spoke to them for several minutes before we eventually found our way to a booth. When the waiter came over to wait on us, he asked how everyone knew each other. I explained that we are all in Chicago for our denomination’s pastors’ conference. I did not think much of my explanation, but his response was "sorry that I asked."  He wasn’t sorry because of my tone, but he was sorry because he felt that none of what I said was relevant to him. He was not rude at all, but it was clear that I had not at all peaked his curiosity.

How could I have responded differently? How could my response have drawn him closer to the Kingdom of God? How could I have peaked his curiosity and encouraged him to ask questions?
During our meal, we had very casual and friendly contact with our waiter, but I believe we failed to salt our conversation in any significant way after he opened the door for us. What would you say?