Dear Steve,

I recently started dating a woman but this is all kind of uncharted territory for me. In addition to being new to this area, I never really entered a serious relationship before. I was a bit of a love ‘em and leave ‘em guy, so the idea of being involved with someone on a more personal level scares me. I know she’s been involved with other men in the past, so what should I expect when this conversation comes up?

Signed,
Walking Gently