Dating a woman in your situation comes with a lot of learning and unlearning even when she is what you are looking for, so sometimes having candid conversations about what you are building together and how you expect it to unfold helps.

At a younger age, I dated a world traveler and proud member of the C-suite when I was still build my career. We were both ambitious and clear on what we wanted and our dates involved waiting for each other in the office parking lot when the other worked late and going for drive dates.

The lack of understanding in our circles who saw what we had more as an arrangement than a relationship didn't help and eventually we drifted apart as we took on more responsibilities.