4 Questions to Ask on a Date: Assess Compatibility & Identify Red Flags

If you’re brave enough to still be in the dating pool, I commend you! It is rough out there, and I respect you for not giving up on finding love!

I speak a lot about compatibility, character, and emotional maturity, so I’m here with some guidance on how to assess for these things. It can take time for red flags to present themselves, and we may not notice them until a real-life situation brings them to the surface.

Today, I’m sharing four questions to ask your date in order to dig beyond the superficial get-to-know-you topics and instead, get to things that really matter. Questions that help you excavate red flags and signs of incompatibility in advance, so you don’t waste your time in the wrong relationship or put your heart at unnecessary risk.

Each question is open-ended and multi-faceted. This allows the conversation to naturally expand and give you a lot of information without much effort. These are questions that both of you need to be able to answer clearly and honestly, so take the time as you go through each question to reflect on your own answers. Also, I encourage you to read through the entire blog post, because I have a helpful resource with a bonus fifth question at the end!

#1 Who is Your Closest Friend, and What Are They Like?

Listen closely to how they answer this question!

First, are they able to name a close friend at all? If they don’t have a close friend, that’s a big problem! It means no one really knows them or has their eye on them. If they can’t name someone, you should ask them why they don’t have a close friend, and see what they say. Usually, it comes down to either they don’t trust people, don’t know how to create and maintain relationships over time, or they aren’t living their life authentically where they’ve found their people. There are significant consequences to this — mainly that there will be a LOT of pressure on you to be their person for everything.

Second, if they do have a close friend, how do they describe them? If they don’t know much about their closest friend, that’s also a big problem! They should know a lot about the person they identify as closest to them. If they don’t have much to say, it tells you the shallowness of their relationship. Friendship is a foundational aspect of any healthy romantic relationship; so if they don’t know how to be a good friend, they won’t know how to be in a romantic relationship.

Ask them how often they connect and what do they do together. Does this friend seem like a positive or negative influence on them? Does it sound like a healthy relationship, or does it sound one dimensional?

Our closest friend is the one we call at our highest and lowest moments; meaning they have a significant influence on our lives. It’s important that you know who that person is for you and for the people you date.

#2 How Do You Spend Your Free Time?

There aren’t a lot of hours in the day, so it’s important that you know what they prioritize.

If they don’t have much free time, they likely won’t have a lot of time to invest in a relationship, so consider whether or not you’re okay with that. If they don’t have an answer for what they do in their free time, it might mean they’re embarrassed of how they spend their time and don’t want to say it outloud.

If they do have an answer, does it align with how you like to spend your free time? There should be some things you can do together, and some separate interests that you rather pursue on your own or with other people. In their answer, do they list things you admire, find interesting, or add to their attractiveness?

Find out what podcasts they listen to, what shows they like to watch, and what books they like to read. Aristotle said, “we are what we repeatedly do”, so these choices of media outline what type of person they’re becoming. Think about whether their media of choice has positive or negative messaging.

We all need entertainment and opportunities to chill. However, if they seem like they’re addicted to screens or mindlessly doom scroll too much, it tells you their focus and energy is not consciously chosen. It means they seek what is entertaining and feels good. It means their attention and time are at the mercy of dopamine. In relationships, that translates to them having a low tolerance for stress, and low level of passion.

#3 How Will You Know You Lived a Good Life?

This is a deep question that tells you a lot about a person. Their answer shows you where they get their sense of significance and what they value most in life.

If they don’t have an answer, it means they are lost with no sense of direction or purpose in their life.

If they do have an answer, does it align with your answer? Is their answer detailed, or is it vague? Do you like what they envision? Are they currently living in alignment with that vision, or describe something that sounds good but has nothing to do with who they are now?

Is their concept of a good life based in something solid like religion, their family values, or contribution to humanity? Furthermore, does their vision of a good life include other people, or just themselves?

Having a shared vision of the future is the map that both of you will be following if you decide to share a life together. Make sure your destinations match!

#4 What Do You Struggle The Most With in Relationships?

This question requires humility, self-awareness, empathy and accountability to answer. All of which are signs of emotional maturity. If you’d like to learn more about the other signs of emotional maturity, check out my previous post, 8 Signs of Emotional Maturity.

NONE of us are perfect, however, it matters that we know what our weak points are. This is similar to the job interview question where they ask what your weaknesses are; it’s actually a bad thing for an interviewee to say, “I have no weaknesses,” or “my weakness is I care too much or I work too hard.”

You should expect to hear and give a clear answer. Some examples include: They have the tendency to be selfish. Or they struggle to communicate how they feel and what they need. Maybe they martyr themselves then get resentful when it isn’t reciprocated. Perhaps they shut down and avoid conflict, or struggle with anger and defensiveness. Some people make assumptions in their head instead of talking directly to the person, while others struggle with boundaries. The list can go on and on…

Plus, there needs to be two follow-up questions: How are you currently working towards bettering yourself in that realm? And can you share some specific examples?

Where Can I Find More Help?

If you’re looking to develop healthy dating and relationship skills — therapy can be a great resource for you!

Maybe you aren’t fully ready for therapy yet — That’s okay too! Click the button below to subscribe to my YouTube Channel, Tips from a Therapist, where I offer some of my best tips on how to improve your relationship with yourself and other people.

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The more you know, the more you grow!