5 Make or Break Questions to Ask on a First Date

by | Sep 22, 2021 | Relationships | 1 comment

In a dimly lit coffee house sit two people, nerves bare and hopes high. First date feelings tend to be mixed between nervousness and excitement. Most people hope that they don’t say too much, do too little, or hide enough. Two people who have decided how much they are going to hide, keep private, or share based on what they are hoping the night turns into.

I gather they have spent a great deal of time deciding what to wear, what to say, and what they should ask or reveal. Most often the idea is don’t talk about sex, the ex, or things that make you vexed. I suppose there is some sensical reason people choose to not show up whole when they meet someone new but I think it reveals more about authenticity and the power of self.

When you walk into a room you should choose to walk in with all parts of yourself and give yourself a real chance at finding external love and acceptance that reflects how you value yourself. So then, what do you do or say in the two hours you will share with a perfect stranger? Everything.

5 Important Questions

  1. Who are you?

So often we ask a person to tell us about themselves rather than asking them who they believe themselves to be. This question is not designed to learn about what a person is or what a person does rather it is to understand and explore the development and expression of a person’s self-schema.

  1. How has shame played a role in your development?

We have experiences that create and help us choose who we are going to be and how we are going to behave. It can be helpful to know how a person has developed their personality.

  1. How did you learn about sex? How do you define sex?

Sex is an integral part of a relationship and can impact the sense of self and the couple’s relationship. It is important to understand how the physical connection was established in early life and what might have carried over into adulthood and what is different now and how that difference evolved. 

  1. What type of conflict have you experienced?

You want to know what frustration, anger, disappointment, joy, love, empathy, compassion, and other emotions and actions look like in a person’s life and how said person might be experienced by others.  

  1. Do you prefer intimacy or autonomy?

This is an important question to ask yourself first. Once you understand your needs around attachment you can begin to create standards and boundaries to help you navigate creating and participating in intimate relationships. Understanding how the partner sitting across from you presents can help you decide if this is a space you want to continue to explore and if so to what depth and definition.

First dates are the first moment you get to challenge yourself to accept yourself. 

As a sex therapist and relationship consultant what I have come to observe is that some people spend time getting to know the external version of themselves and others. Many may present with a lack of a sense of self and may depend on information about themselves from others. In addition, that makes it challenging when it comes to connecting with a potential partner. This is often because we are not sure of what it means to trust ourselves and therefore feel the decision process may be flawed.

Here are a few books that have been helpful on this topic:

What I have found is that the five questions above offer an opportunity for depth, openness, vulnerability, intimacy, and sincerity. All traits are necessary for intrapersonal and interpersonal growth. And a clear understanding of each assists in learning quickly whether a first date would be worth continuing.


Count on Kiss & Tell Magazine to continue the discussion on women’s issuesrelationships, and sexual wellness. Subscribe to our weekly newsletter below and always be part of the K&T community.

Like K&T AND share by clicking one of the social buttons below or by copying the link.

Aje Global