He has this policy because years ago when pastoring our first church he and I were standing at the back doors greeting people and a lady came through who looked pregnant. Her overall body was very small, in fact from the back she just looked like a skinny woman. But in front her stomach protruded so much, almost like a basketball, that she looked very pregnant. As she was coming through Larry said, "Oh, when are you expecting?" She looked very offended and said, "Expecting WHAT??!!"
Knowing him he probably shot back something like, "Expecting God to do something in you life," or something like that to get him out of that mess.
After church he said, "I will never ask any woman that question again no matter how pregnant she looks." Conversely this has resulted in some strange looks when he meets genuinely pregnant women who are obviously so and they say things to him like, "We're having a girl," and he says, "Oh...you're expecting?" and they look at him like, "Duh...are you blind? What did you think this was... a basketball under here?"
Actually he uses me as his spy in this regard. When a new lady comes to the church and she appears to be expecting he always asks me to find out for sure and report back to him. Yes, a co-pastor sometimes serves as an undercover agent.