There are two ways to date: intentionally or casually. Now that may seem like a leading statement so I want to be clear: casual dating can result in long-term, healthy relationships in addition to short-term, fun-filled flings.
That said, people who date casually often end up somewhere in between, in situationships that tend to drag on longer than they should. You may get lucky and your situationship ‘partner’ may happen to share enough of your core values–one of which could be tolerance for different values–for the relationship to flourish, but…how likely is that? And more importantly why leave it up to chance? Why waste your time when the pool of potential life-partners decreases each year?
Of course, it does take time to truly get to know someone, but you can learn some decisive things on a first date…with the help of good questions.
What makes a question good? To be a good question, it must either:
- stimulate the other person (which makes you more attractive in their eyes)
- reveal the other person’s core values (which helps you both assess fit)
A good question often does both of these things, but this post is going to focus on questions aimed at revealing your dates core values. However, before we create a list of probing questions we need to understand what to probe for—what are you looking for in a partner?
This is one of the more difficult questions we have to answer in life and experience is necessary to teach us what we truly need (vs think we need). I don’t have a framework to help think about your ideal partner (yet?), but will share some of the values I look for on a first date:
- Physical Health: does this person understand the importance of physical well-being and have a habit of daily exercise? I don’t need my partner to be a world-class athlete, but I don’t want to become a caretaker prematurely
- Self-Actualization: does this person have concrete dreams and actionable goals? Do they want to get better? Do they have a growth mindset? Life is long and I want a partner who has goals beyond marriage and kids
- Curiosity: does this person want to know the ‘why’ behind things and have the ability to gain insight on their own?
- Financial Independence: I want to retire early so it’s important my partner does not significantly delay that dream…even better if they can help!
- Humor: I personally can’t imagine a worse life than one without playfulness and laughter
Now it’s time to make your list. Do not skip this step because how do you expect to find someone if you don’t know what you are looking for?
As you make your list, strive to be as open–minded as possible–does your partner really need to share all your hobbies or root for your favorite sports team?
Your list should be SHORT (try to keep it to 5 or less core values) because humans are generally pretty poor at predicting what will make us happy (there are numerous studies and books on this). Bezos is a schmuck, but his philosophy of ‘stubborn on vision, but flexible on details’ is apropos here.
Once you have made your list (did you make your list?), it should be easy to create some questions that help reveal whether you and your date could be a good fit. My list looks like (less is more):
- What do you do to stay active?
- Do you like your job? If not, what’s your plan to do something else?
- Would you want to be a stay-at-home parent?
- What are some of your current goals?
- Where do you get new ideas from?
- What do you think happens after death?
- Do you think love is more of a choice or a feeling?
If this feels like too much work, just take 1-2 questions from my list to add to your pre-date checklist. If you find the questions illuminating, then return to this post and create a few of your own.
Also, despite everything I’ve said, remain open to the idea that you are wrong about what you think you need. Just because your gut can lie, does not mean it is lying. If you have a very strong feeling about someone–despite perceived significant differences–then I’d advise you to see it through. You may look back at that decision as a foolish mistake, but it may also be the start of something wonderful! Besides, to err is human, a life without mistakes is a tragedy…
tl;dr Life is short. Dating is hard. Ask good questions.