When I left my marriage, I thought I knew exactly what I wanted to find in a man. My analytical mind had been assessing what I could bring to a romantic partner and what I wanted from them through nearly every moment of my 20-year relationship. Yet, as I dip my toes into the dating pool, I’m learning that I actually like some of the things I thought I disliked, and vice versa.

The ties that bind between parent and child are always complicated, often wondrous, and—as Sheila discovers—somewhat inexplicable.

I find myself dating for the first time since I was 21 years old. It turns out that my experience of vetting thousands of entrepreneurs over the past decade as a venture capitalist is coming in handy. Especially when it comes to trusting my intuition.