Top 7 Second Date Questions (And Why You Should Ask Them)

Love is like a virus. It can happen to anybody at any time.

- Maya Angelou

---

As a Seattle based dating coach and consultant, I am frequently approached by earnest, well-educated individuals looking for real love.

So many daters these days appear to be supplanting the substantive, slow-cooked intimacy narratives of yore with the relationship equivalent of fast food.

We prefer chemistry over connection. And it needs to be easy, hot, and now.

This can be a real drag for those of us looking to move past a first hookup and on to the complicated process of getting to know the person sitting across from us.

The ability to feel and express emotions is unique to human beings. It is what distinguishes us from lizards. The mutual exchange of feelings is also one of the core components of real intimacy.

So what do we do once we've surpassed the scripted “getting to know you” conversations associated with a first date?

Here are seven questions that will help you coax your second date conversation toward the deep end of the pool:

1. When is the last time you cried? This question will provide you with a hint about your date’s level of emotional sensitivity. Be cautious of those who say they don’t cry. People who don't allow for the healthy expression of sadness are often skilled at heaping it onto other people (which could be you someday).
2. What subject or activity makes you lose track of time? A well-rounded individual should have at least one thing they care about. People are more likely to feel attractive and be attracted to someone when they are talking about their personal passions.
3. If you could change anything about yourself, what would it be? You must pinky swear me that you will think long and hard before accepting a third date with someone who cannot think of at least one thing about him or herself s/he would change if s/he could. Humility is a sign of maturity. Arrogance is not.
4. What are the top three most defining moments in your life? Our most poignant memories illustrate the relationship we've formed with ourselves. The answer to this question can also speak to your date’s values (accomplishment, resilience, etc.).
5. If you could go back and do anything in your life over again, what would it be? This question addresses your date’s ability to learn from past mistakes--an essential part of conflict-resolution in a long-term relationship.
6. Who was your favorite family member and why? Family relationships form the template for adult relationships. Finding out about the person to whom your date felt closest in his/her family allows you to see what values and traits your date will be drawn to in a partner.
7. What is the scariest thing you’ve ever done? Courage is not the absence of fear. It’s the willingness to feel afraid and do it anyway. Asking this question will help you asses your potential mate’s ability to stretch outside of his/her comfort zone and learn new things.

​There is a time and place for lighthearted, superficial banter. It’s a necessary part of getting to know someone. But, once the small talk has been folded and packed away, these questions will help you take your second (or third or fourth) date to the next level.

And remember: the cornerstone of intimacy is the reciprocal exchange of sentiments. Ask only the questions you’re willing to answer yourself.

What about you? What are some of the best out-of-the ordinary questions you’ve said or encountered on a date date? Leave a comment and let us know!

Dr. Jill Gross is a licensed psychologist, counselor and dating coach in Seattle, Washington. Find out more about how hiring a dating coach can help you have a richer, more satisfying relationship experience. Schedule a free dating consultation today!

Schedule Your Free Consultation Now

---