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Dating & Relationships

5 Questions To Ask On A First Date

Do not go on another date until you have read this post or watched the YouTube Video!

Have you been on a second or third date and thought, “Oh wow, how did I miss that red flag? This is not going to work out!” Wasting your time on someone that is not a fit for you sucks. It especially sucks when it’s weeks or months down the line and you realize you haven’t gotten to know the important things about this person, and when you do find out, they end up being your non-negotiatbales.

Dating for anyone is hard, and dating as a digital nomad comes with it’s own set of additional challenges. Dating as a digital nomad means that you typically have less information about this person since you are both traveling and likely met in a location where neither of you have many deep established connections, unlike location dependent people who have strong community ties and possibly more friends in common. It is possible but less likely to have some friends in common and connections with the community. Digital nomad couples also have less time to figure out compatibility during dating before one or or both of them is off to the next destination. The worst is when you change your travel plans or home base location for someone you think is the one, only to realize that you didn’t do your homework on them well!

That is why I am gifting you 5 questions to ask on a first date. Relax, I am not going to suggest you ask their date, time and place of birth to figure out their astrology chart. I am not going to suggest that you request a bank statement and a reference from their previous relationships, although all of those pieces of info would be super helpful! When going on a first date, we want to keep it light, fun and casual, but we also want to find out if this person is worth seeing again. Getting to know real information about you date can help you make quicker decisions about how you want to spend your time and energy going forward.

What’s In A First Date?

Often people who date focus on two main categories: Emotional and Physical. We initially date someone if we think they are attractive (Physical) and if they make us feel some sort of way (Emotional). But that is not the only information you need in order to make a good decision on compatibility long term. Pivot, the relational alignment curriculum I teach from as a relationship coach, tells us that there are 5 main categories that make up life, and so I am giving you one fun and easy question for each category that will give you major insights into compatibility right away.

These questions will help you flesh out red flags and see where your preferences and non-negotiatables align. This works best if you already know what red flags to look for and what your non-negotiatbales are, so before you try this out, read the related blog on spotting red flags also! Like the Pivot Whole Perspective framework, I have broken our questions into these categories: Financial, Spiritual, Emotional, Physical, and Intellectual. Let’s get to it!


The Question: What do you like to spend money on?

Why it works: You will get a range of answers from “i don’t like to spend money” to “I spend money on lots of things”. You wont likely get a good sense of their financial portfolio like how much they make, how much they are worth, how much debt they have, and how much savings they have, but you will get a good sense of their financial habits and behaviors. You will learn what things are priorities for them and what things are not.

Depending on the price of the splurge, you may get insight on the budget they operate from. You may want to ask some follow up questions like “how often do you get to spend money on that”. You are looking for common shared values here. Are their financial behaviors similar to yours? If their big splurge was a wine subscription or a trip to a distillery yet you are in sobriety, then there is an obvious mismatch in values here. If the splurge was on family and friends, this may also raise concerns around boundaries and capacity. Were there any red flags in their answers? Make a mental note to look for and ask more clarifying questions at another time.


The Question: What is your favorite holiday?

Why it works: Most holidays are inherently religious. If this person has a strong opinion about a religion they will likely offer it up with this question. They will say oh man I hate Christmas because” … or they may say “I love going to church with my family on Christmas Eve”. They may say “I love Halloween where I can be my witchy self.” They may even tell you any bad experiences they have had with holidays in the past: “not Valentines day.. ugg my last Valentines day was a disaster.” Deviations on religious practices are often big cultural differences that matter and should be discussed early on.

Depending on your values and the qualities you are looking for, you will be able to gain a lot of insight on compatibility. You will also get a sense of if they love to celebrate by going all out, if they have a big family and love to be around them, or if they prefer quiet holidays in their own space. You may even get an idea of if they have or want children from this question.

This question will not get you too far into the spiritual beliefs and practices that this person holds, but it will give you a baseline for them. You may ask some follow up questions about how they like to express their spirituality on a next date.


The Question: How do you like to manage your stress?

Why It works: I love this sneaky question. In essence I am looking for what tools and strategies this person knows and uses to self-soothe and repair during conflict. I am listening for wether they are doing a routine practice, if they feel in control of their time, and if they are taking radical responsibility for their emotional wellbeing. If this person dumps on you about how they don’t have time for stress management or if they really unload about all the things that stress them out.. RED FLAGS. You will get a read on emotional intelligence, awareness, and capacity also. Does this person even have time and energy for a relationship right now?

You may also get a glimpse in to some unhealthy coping strategies, like if they say something about alcohol or weed (not that these are inherently bad, but they do not go into the stress management category as far as I am concerned). Another thing you may get here is a read on their emotional support system. They may say something about a best friend or a sibling that they go to in stressful times.


The Question: How do you like to spend your time?

Why It Works: This is a tricky one to get a read on. What we want to know here is two fold: Location and Physique. Location is about where they spend their time like how many hours do they dedicate to work, do they exercise, go to the gym, hang with friends, spend time in nature or in another physical location. Physique is how they see themselves and others physically. From this question you may get a read on wether they are introverted or extraverted.

You may get a read on their priorities. You may get to know what frustrates them about their location and time spent (if they like where they are or if they would rather live somewhere else). What you don’t get with this question is if they like their physical body and if they have any limiting or damaging beliefs about physique and body health that could be red flags. Those are things you will want to look for and ask about on another date.

If they are nomadic, you may get a timeline of where they plan to travel in the next season of life, which is really important in vetting compatibility.


The Question: what is the coolest thing you learned this past year?

Why it works: I think this question is the most fun of the five questions. With this question you will get a sense of how they like to learn; did they learn this thing in a group or solo? Was it by reading, watching, listening or doing? How long did it take them? What was their commitment to it? You will get a sense of what topics are interesting, important, exciting and fun for them. You will get insight into how much time they spend learning and you might even get what they are looking forward to learning more of in the future. If they are entrepreneurial you may even get what they are building in their business and excited to add to their business going forward.

If you are dates, weeks, months, or even years passed this.. give the questions a try anyway. This could be a great date night and a way to deepen your relationship together.

Does The Thought of Dating Give You Hives?

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