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Rachel Zwell | June 10, 2015

How to Know Which
Questions to Ask
on a First Date

Going on first dates (whether paired up by mutual friends or an Internet dating site) is bound to be a bit awkward.

Hey, meeting anyone for the time can sometimes be a little difficult! Many people wonder what questions they should ask their date to determine if it’s a potential match (…aside from the typical: “Where are you from?” and “What do you do?” stuff).

Ask Yourself Some Questions First

The truth is, there’s no one right or wrong question to ask. Instead, you need to ask yourself some important questions first. Think about what core values you’re searching for in a potential mate and relationship. First, think about what you’re looking for. Are you looking for casual dating, or a lifelong relationship? Understanding yourself and what you’re yearning for increases your chances of getting it! For example, one of my core values is honesty. Sometimes I ask my dates what their impression of me is. From their answers, I can tell whether they are willing to take risks and tell the truth, or whether they tend toward superficial, easy, “nice” conversation. It helps me to get a sense as to whether they share my values system.

Don’t Be Scared to be Direct

Super-direct questions such as, “Why are you dating?” or “What are you looking for in a relationship?” can seem intense. Some people may be uncomfortable with this approach. (What if the other person is weirded out or thinks I’m coming on too strong?) Don’t sweat it. Your ability to ask the tough questions is actually about empowering yourself and allowing yourself to get what you want. Instead of playing all of those guessing games that tend to go along with the dating world, be direct right out of the gate to save yourself some time and more pain later.

Truly Listen to your Date’s Answers and Stay Authentic

Asking a lot of questions on first dates can also help lead you to understand your own deeper wanting and yearning. Certain questions may heed different results and will help you understand what’s actually important to you. Don’t be afraid to be a warrior: have high expectations. There’s something you want out of connections with people and you deserve to be satisfied. Be your authentic self on dates. When I’m afraid to be truthful and authentic on a date, it’s often because I’m afraid of being rejected. The thing is, I don’t truly want to end up in a relationship where I’m not being myself! I would rather be known for my true opinions, thoughts, and feelings, and eventually be in a relationship with someone who values who I really am—even if it takes a little longer.

What If I Don’t Want to be Direct Right Away?

Some people may be shy at first—I know I can be! Perhaps you‘re afraid to ask direct questions until you’re a little more comfortable with the person. The point is to be direct even when you’re afraid. We’re all dating with the goal of a connection with another human being. Playing a game while not being authentic will only end with a greater loss. Sure, putting yourself out there and being authentic is a risk—you’re definitely getting out of your comfort zone. But ask yourself, “What’s blocking me from engaging in the here and now? How can I get the support I need to take risks and ask the direct questions?” Discover these answers and you may be willing to up the ante. For example, do you have any deal breakers? Ask about it upfront and then decide how you feel about their answer.

What If I Feel I Don’t Like the Person at the Beginning of the Date?

Create value for yourself anyway! Even if you’re totally sure you’re not interested, you can still learn something about yourself and have a connection with another human being. Ask more questions. Maybe you will learn about what you like…or dislike. At the end of the date, whether you decide to meet again or not, at least you’ve given yourself the opportunity to put yourself out there and learn more about what you’re looking for in another person. Put away those snap judgments and allow yourself to be curious and present in the date.


All in all, being your authentic self and initiating open and honest communication from the start sets up positive expectations for relationships.


Hey, it’s ok to go on a lot of first dates! The idea is to meet new people and get to know yourself in the process. Meeting someone great should just be a bonus! Have fun!

For more ways to understand what you truly desire in life, visit Wright Now. We offer an array of courses geared to help you learn more about yourself, your career, and your relationships. So don’t miss out on the life you want. Start today!

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Image courtesy:Flickr user PhotoSteve101


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.


The Wright Foundation for the Realization of Human Potential is 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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