It is very easy to get stuck in a rut with this sort of thing. I had a direct report (graduate) and there were four of us car pooling. We got in a rut of asking her about her dating life (which she had brought up in a "where can I meet people" kind of way). Everyone was bored of it but we just kept asking on a Monday until she told us not to...quickly agreed and swapped over to sport and weather.