After leaving my marriage a year ago, I find myself dating for the first time since I was 21 years old. While a dating novice, I’m finding that my experience of vetting thousands of entrepreneurs over the past decade as a venture capitalist is coming in handy. Perhaps one of the most important lessons I learned as a VC is that intuition matters. I often knew whether to invest in a startup by the end of the first meeting. The opportunities I passed on were the ones that “felt right” but looked bad on paper, and my bad investments were the opposite. I’ve learned a lot by paying attention to my intuition from the onset and continuing to reflect and re-assess by continuing to listen to my intuition. With that in mind, these are the questions I will be asking myself when I first meet and continue to get to know potential mates.
1. If I forget all of the facts I know about this person, how strong is my natural desire to spend more time with them?
2. If I let go of all of my preconceived notions about what I am looking for in a partner, how much of a desire do I have to be close to this person?
3. If I imagine my gut feeling about this person is correct and I had to make the decision of whether to marry this person today, what would my answer be?
4. On a scale of 1-10, how certain do I feel about that answer?
5. If I had to make a decision of whether to marry this person today or be single for the rest of my life, would that change my answer?
6. On a scale of 1-10, how upset would I be if I:
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- never saw this person again?
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- had to spend the rest of my life with this person?
7. Does it feel as if this person could accept me exactly as I am?
8. Do I feel as if I could accept this person exactly as they are?
9. On a scale of 1-10, how much permission do I feel to be my authentic self when I am with them?
And because I LOVE asking questions, here are a few non-intuition-based questions I like to ask, as well:
10. It is often easy to see why this relationship won’t work, but what could unfold if it goes right? (This is the most important question I learned to ask as a VC. Read my blog post “What If Everything Goes Right Rather than Wrong” for more of my thoughts on this.)
11. What, if anything, have I learned about myself from spending time with this person?
12. What, if anything, have I learned in general from spending time with this person?
13. On a scale of 1-10, how much do I want to be physically intimate with this person?
14. Did our conversation feel effortless?
15. In what ways does their personality complement my weaknesses?
16. In what ways does their personality complement my strengths?
