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Rachel Zwell | January 28, 2016

What Questions Should
I Ask on a First Date?

Don’t you wish there was a script for first dates? A standard set of screening questions? Have you ever seen the article circulating online detailing 36 questions YOU should ask to “find love”?


We’ve all read magazine articles like this before—promising the perfect interaction and happily ever after if we just screen with the right set of questions.

In reality, there’s no tried-and-true questionnaire for screening your dates. In online dating profiles, we do get the answers to some questions. But not all of us meet our dates online. What about the girl you approach at the gym or the guy you meet at a networking event? You can’t exactly ask them to fill out a match.com profile on the spot, just to see if you’re compatible.

It’s easy to make snap judgments when we walk in on a date. We look at how our date is dressed, we evaluate their jewelry and their habits, and we immediately have a reaction. Maybe his glasses remind you of your dad or her perfume reminds you FAR too much of the coworker who drives you nuts.

The truth about first dates: To have a successful first date (and a successful fifty-first date)—it’s all about what you put into it! What does a successful first date look like, anyway? I consider it a good date if I’m enjoying my own company, learning something new from my date, and learning about myself. When you’re fully engaged, expressing your yearnings, and being up front and honest about who you are, you can discover more about yourself and others—even if you don’t feel a romantic connection.

This ISN’T a Great Date

Sometimes “bad dates” can teach us more about ourselves than the great ones. The next time you’re on a date that seems to be going awry, ask yourself what’s really bothering you about your date.

Maybe he’s rude. Maybe she talks incessantly about herself. Maybe she’s condescending. Whatever it is, allow yourself to be fully IN the situation. Let your date know what’s bothering you, and see what you can learn from the interaction. It will tell you a great deal about how you handle being uncomfortable and the ways you shy away from or engage in conflict.

Not every date is a perfect match, but every date is an opportunity. Part of the joy and fun of dating is getting to know different people and getting to know yourself. If something bothers you, explore what’s going on with you!

This IS a Great Date

Many times, first dates might actually be going well, yet we find ourselves holding back. Maybe you don’t ask the hard questions because you’re having fun: you’re attracted to your date and enjoying your time together. Maybe you don’t want to scare them away by bringing up big topics like babies, houses, and marriage. Maybe you don’t want to find out they’re a homebody when you’re an adventurer.

Here’s the truth: a first date is a great time to ask anything! You haven’t fully invested your time, effort, and energy into the relationship yet. It’s a great time to find out if you’re on the same page and working toward the same outcomes so you can continue. Why wait until you’re six or seven dates in, only to be disappointed that you’re not really jiving on some of your biggest yearnings?

Some of us go into our first dates with our tough question ready—guns a-blazin’. We’ll ask anything, engage in conflict, and figure out what page they’re on. THEN, as time goes on and we become more emotionally invested in the relationship, we start holding ourselves back. By then, we’ve put our emotions and heart into the relationship, so we don’t want to be crushed when we get an answer we don’t want.

Relationships Are About Continued Engagement

In The Heart of the Fight, we talk about how you can continue to discuss and bring up your yearnings, engage in conflict, and keep the communication flowing throughout your entire relationship. For the first TEN YEARS or more, you’re trying to find your footing and you’re vying for control and understanding. Face it: if you’re in it for the long haul, you’re going to address these issues. Putting them off is just staving off the inevitable.

Dating is such an amazing opportunity to get to know yourself and someone else. It’s exciting to engage with someone and to learn more about your reactions—what you like, what you don’t like, and how you feel. Allow yourself to go off-script and get down to discussing what really matters to you. You’ll feel better about the relationship if you like who you are being. I want to be someone who takes risks, who tells the truth, and who gets to know myself better with each date.

Let us know how your dating is going! Tune in to our podcast every Wednesday to talk about dating, relationships, and how to bring out your best self. To continue the conversation on engaging with others and to discover ways to bring out your best self, click here to learn more about our next More Life Training.

Listen to this episode here on BlogTalkRadio or here on iTunes.

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About the Author

Rachel Zwell

Rachel is a Coach and Executive Assistant to the CEO at Wright. She specializes in coaching adolescents, helping them navigate young adulthood and grow into their gifts and leadership. Rachel is responsible for leading and facilitating groups during weekend trainings. Currently, Rachel is pursuing her master’s in Transformational Leadership and Coaching from the Wright Graduate University.


Blog image courtesy Flickr user dickuhne.

Wright Living is a division of the Wright Foundation for the Realization of Human Potential, a leadership institute located in Chicago, Illinois. Wright Living performative learning programs are integrated into the curriculum at Wright Graduate University.

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