Regardless of how you want to look at it, first dates are like job interviews. First impressions mean everything and we are quick to make judgements based on the entire package we are presented. Consciously and subconsciously, our eyes will scan the outward appearance, notice the body language, and make judgements on the speech and words being said. If this first encountered resulted from meeting online, then this person will be referenced to their online profile and preconceived judgments have already been made.
I personally found the online dating process to be exhausting and in an effort to reduce wasted time and hopes on a person’s potential, I put my psychology skills to good use in combination with my skill of being a good conversationalist.
I hope by this point I didn’t offend too many people. I understand that social anxiety, having an off day, and the very idea of being judged can be triggering, but in reality humans are constantly making judgement calls. Life is short and if there is a possibility to be in an ideal partnership sooner, then this article offers a strategy for that through communication. Having good emotional intimacy through communication is not essential for everyone when it comes to romantic connection, but for me and others that I know, it is foundational.
With that in mind, these questions sound pretty simple and but could tell you a lot about a person if you know how to look for the deeper meaning. These questions sound a little dry so spice them up to fit your personality and allow for conversation to flow rather than going down a list of questions. Prepare for your date by selecting questions that align most closely with your values and what you are looking for. These questions are designed to help someone looking for a committed relationship, or longterm friend, not a quick hookup.
- How do you like to spend your free time? This gives you a glimpse at their passions, their levels of introversion or extroversion, and how interesting they are.
- What are you currently excited about or working towards? This reveals how ambitious they are. How growth minded, and interested they are in learning. Maybe they are in a period of transition, so in this case you can explore something they have worked towards before that excited them. This reveals if whether you being in a relationship with them is the best idea for both of you based on your goals and current life trajectory.
- If money weren’t an issue, what would you be doing with your time? This gives you a deeper glimpse into their passions. Whether they prefer to live a more relaxed or more spontaneous lifestyle. If they are altruistic in nature. How grand their vision of desired achievement is and potentially what direction they are trying to go.
- What do you like most about yourself? This reveals their level of self worth, self esteem, confidence (or potential narcism).
- What are some obscure things that you are or were really into? Everyone has a level of weirdness they either are comfortable sharing or not sharing. Usually the truth comes out after being together for a long time, but maybe there is something they are comfortable revealing that may either captivate you or be an immediate red flag.
- What is an accomplishment you are most proud of? This gives you insight on their values and main interests. If they are career driven that does not mean they wouldn’t be a good romantic partner, but if they define their sense of worth on their career accomplishments then maybe they will continue to pour their energy there and be more closed off emotionally.
- What are the most important things to you? This question reveals their values. How materialistic they are. If they are more internally or externally motivated, such as needing to be perceived a certain way by people verses feeling adequate regardless.
- If you had to imagine the perfect adventure, or maybe remember one that you experienced, how does it go? This gives you glimpse into their imagination. How daring or safe they live their life. How much freedom they currently have. If they prefer a more off the beaten path or concrete lifestyle when they travel. If they like a more lavish or humble adventure.
- What would your perfect day look like? This may give you an idea of what they are looking for, if they are comfortable spending time alone, or where they are at currently in relation to their vision.
- Where do you think we go after we die? If you are someone who likes to philosophize and go deep into conversation about the meaning of life, then this question will surely reveal how interested they are in that respect, and also if you are religious and value a partnership with someone who shares similar views. This is a fairly out there question though so choose an opportune moment to ask it, perhaps in a place you can both clearly hear each other and the conversation seems to be flowing in that direction already.
- If you could be any superhero who would you be and why? This explores their level of imagination, if they are in touch with their inner child, and what does power (or control) look like to them.
- Do you know your love language? If they know their love language then they probably have been in committed relationship or have an interest in the topic of enhancing relationships. If they don’t know it, sharing a quick summary could lead to an interesting conversation.
- What’s your view on monogamy? It is no longer safe to assume that everyone agrees with monogamy when it comes to modern dating. This question is reasonable to ask and very revealing on where someone stands in how they perceive the difference between love and lust.
- What is your zodiac sign? If you use astrology to gauge compatibility then this question reveals how open minded they are with topics pertaining to this realm.
- What do you find most attractive about a woman/man/person? Attraction builds chemistry so it is good to know whether you have the qualities they are attracted to, whether that is internal or external.
- What are you looking for right now in regards to dating and relationships? This is quite a direct question and one I would save for the end of the night or following date. They don’t have to know the answer then and there but it is good for you to be comfortable with voicing what your intentions are. A question like this has the potential to weed out the Don Juans from the boyfriend/girlfriend types.
- What did you learn about yourself in previous relationships? This question reveals whether they have a good judge of character or if they tend to attract the wrong people to them. It gives you a glimpse at how guarded they are based on the outcome of previous relationships and if they are capable of admitting their faults and growth areas. A person who says, “all my exes are crazy” should be approached with caution because either they are repeating a trauma cycle from inconsistent caregivers or they displace their own limitations on everyone else.
Thank you for writing this! I love how you unpack and present what all we can learn from each question.