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7 Questions To Ask On A First Date

2020 has been challenging for love, intimacy, and forging new relationships. This new year, we're kicking off dating on the right foot.

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These 7 questions can help kick off dating in the new year on the right foot. 2020 has been challenging for love, intimacy, and forging new relationships. We have been asked to date in an entirely new way. Whilst I predict we will always need and thrive in human physical contact, in the interim we must make some very short-term adjustments. This means focusing on the opportunity, not the problem. We can get to know each other at deeper levels and get clearer on the types of relationships we want to have in 2021 and moving forward.

Data demonstrates that most New Year resolutions fail by around January 17th. If finding and creating epic love is your New Year resolution, here’s how to have an empowering start to your new year of love, intimacy, and great sex! Now, are you wondering how to know if he is right for you, or are you wondering why it is essential to know which questions to ask on a first date? Asking the right questions helps you connect and understand the other person at a deeper level, which will benefit the relationship to the next level!

Nobody wants to waste time and give their energy away to someone who doesn’t resonate with us. Particularly over the holiday season (such as Christmas), some of us can feel lonely. In that sense of loneliness, we make decisions that come from desperation or fear of being alone. It is crucial here that we be discerning, trust our judgment, and take our time. Powerful questions can help with being more self-honoring and connected to your truth. 

A lot of people ask me, “When do I go deep? Really deep? I am really ready, and I also don’t want to be alone. I don’t want to scare him or her away, though.” I understand why people are so worried. We don’t want to go too deep, too fast, AND we don’t want to be alone. We have to enjoy the lightness, the playfulness, that comes with meeting new people and trust that the decisions we make for ourselves matter.

People go on a date for a reason. They are genuinely curious about and have a good feel for the person they share this critical moment with. We have to lean into the conversation and be present to what the other person has to say, or in this case, how they answer your questions. Ask questions from a place of vulnerability and openness. You may also respond to your questions.

The following are great questions to ask to tap into the mind of a potential partner:

1.)   What are your top 5 values?

It’s great to know what the other person thinks is important in life, what drives them, what inspires them to live a productive and connected life. It would also be interesting to hear them speak about the things that they want in life, their dreams, and their aspirations. This will give you an idea if you’re (mostly) in alignment.

 2.)   Describe your relationship with your parents/primary caregiver.

Did they have a happy childhood? A sad childhood? How the other person speaks about his

or her guardians speak volumes about how they handle themselves and how they handle life in general.

3.)   What is your most favorite memory/experience from childhood?

Observe how the other person’s face lights up when speaking about a happy or fun memory or how their eyes would suddenly reflect sadness, perhaps indicating past trauma or unresolved wounding. It can even tell you a little bit about what the other person might also be suppressing.

4.)   What is one of the biggest challenges you overcame, and how did you do it?

Pay attention to the nuances of the language. Did it benefit just the person, or did it help many? Does the story sound selfish or inclusive and collaborative? What approach was taken in overcoming the challenge, and what did the challenge mean to them? How did it affect their life? Notice if the person is integrating emotional constructs, emotional expression, and vulnerability and notice to what level of detail they will tell you that they can be reflective and expressive in other aspects of your potential relationship.

5.)   What is your greatest fear?

Most significantly, the masculine will struggle to express fear because they struggle to be vulnerable for biological and cultural reasons. Notice how vulnerable and emotionally expressive, emotionally intelligent, or emotionally mature he is here in terms of how he can access expressions within himself – particularly fear. Men will often want to mask fear with anger or frustration, or some other secondary emotion because accessing fear can be confronting for them. This is especially true because they haven’t been taught how to emote, which gives you an idea of how he grew up. Did he grow up to express his emotions healthily and not in a leaky, watery way? Does he suppress, or is he overly expressive? That can be a sign that maybe he’s too immature with his emotions, and he hasn’t got a hold or a container on them? Also, an indication of how he may deal with difficult situations in the present.

6.)   What is your biggest dream in life?

You want to see how excited and connect they are to their purpose and how clear the vision is that they have for themselves. This can indicate confidence, which can be very attractive. You also want to know how it relates to the life you are pursuing. If this person wishes to backpack around the world for three years and you’re ready to settle and ground, perhaps having a family, then maybe your priorities are different.

7.)   What’s the “worst” thing you have done, and what did you learn from it?

It would be interesting to see how deeply the other person goes into expressing this. Is there remorse around it? Is there guilt? Notice how deeply they can tap into the emotional construct of what they did and how it affected them and the people around them. How do they even define “worse”? Does it sound like the person learned something valuable from experience? This will give you an idea of how carefully they have thought about the issue and how much pain it has brought to their life and the lives of others. Are they going to make those same choices again or have they really grown from it all? 

Observe and notice their reactions, body language, expressions, the level of clarity, and intelligence by which they tell their stories. This will give great insight into how a person is and if your and their values are in alignment. The most important thing about all this is knowing and getting clear on what YOU want, what your values and non-negotiables are, and what you are expecting to manifest in the relationship. Be open and willing to learn, be curious, and even ask more questions. Most of all, have fun!

One is glad to be of service.

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