7 Key Questions to Ask on the First 3 Dates

Here’s a quick test to help you determine if you’re truly ready to go after your goal of having a long-term, successful relationship:

Picture this: You’re on the 3rd date with someone you really like – and who seems to like you. Can you imagine yourself saying something along these lines?
I think it’s pretty clear we like one another – and I think you’re a terrific guy/gal. As we talked about on our last date, we’re both interested in finding someone to be in a long-term relationship with. If we’re going to continue dating, I think it’s a good idea to share with each other what we envision for ourselves to further test our compatibility. Would you be open to talking about that?

Yikes, right?

You’d be surprised. It’s actually not a tough question for people who are both ready to be in a relationship and relatively confident and clear about what they want and need. This type of person understands it could take time to find the right partner. So even when there’s chemistry with someone, they believe it makes sense to ask the difficult questions early on to make sure their relationship values and goals match up.

What might seem like the Mt. Everest of questions is also easy to leapfrog for those whose life goals, (i.e., marriage and family) are tied to age. Many like-minded folks in their 30s and 40s have already dated a lot and are ready to make a decision on a partner. And don’t think biological clocks just affect women. Even though men may be capable of fathering a child at age 60 doesn’t mean they want to wait until then to do so.

The “7 key questions in 3 dates” timeline this post proposes isn’t for everyone – nor is it even appropriate for everyone.

If you’re in your early 20s or just want a casual relationship, then taking it slow and letting a relationship evolve organically is to be encouraged. On the other hand, I have a 55-year-old client who hasn’t dated in 8 years. Since she doesn’t want marriage or children, she’s absolutely fine with taking her time so she can uncover what (and who) feels right for her.

In between these two camps, there are many people who truly, (and perhaps desperately) want to be in a relationship yet always seem to get tripped up by common dating pitfalls like fun-but-futureless serial dating or ending up with the wrong type of partner…again.

These people suffer, but I believe there’s a way to end the pain. More about that at the end of the post.

But first, here’s why I believe there are 7 key questions serious daters should ask on the first 3 dates!

I like to compare the first few dates with someone to how we typically size up a buffet line. Think about it. Most of us stroll up and down the table, seeing what looks good before deciding what to commit to our plates. Why? Because if we simply selected the first several items on the table – we could end up missing the really yummy and satisfying entrees further down the line!

That’s how I lay out my 7-questions approach to my relationship-coaching clients. I encourage them to look at dating as a way to get clear about a person’s rightness for you before you’re in too deep. If you take the approach to let things “develop organically,” you could end up spending a lot of time with someone, only to find out they’re not someone you can be with long-term.

Plus, asking the key questions early on can save some heartache. Many people, women in particular, have a hard time letting go of a relationship once there is physical and/or emotional intimacy. So even if you come to know that he or she can’t meet your needs, it can be hard to say goodbye to someone you’ve really connected with.

One final note before the questions themselves:

I’m not proposing that these are the only questions you’ll ask, (or answer) on dates 1, 2 and 3. You’ve gotten to know hundreds, perhaps thousands of people in your lifetime, and that aspect of dating is no different. But if you’re nervous or unsure, a quick trip to the Internet will provide ample first-date conversational tips.

OK. As promised, here are the 7 key questions that will help you move on to the next date – or simply move on.

Date #1
1. What do you do for fun or as hobbies? Do you prefer adventurous or quieter activities?

This icebreaker is perfect for discovering if there are any interests you share, which is an important aspect of healthy relationships. Of course there is nothing wrong with having dis-similar interests, too, as they help people develop their individuality within a relationship. There are no right or wrong answers here; you’re simply looking for a sense of your date’s temperament and personality.

2. What should I know about you that I’d never think to ask about?
3. What do you wish people would stop asking you?

People aren’t generally asked these questions, so they have to think about their answers. You can learn a lot from their verbal – and nonverbal – responses. For example:

  • Do they get defensive or are they intrigued?
  • Do they give themselves the time they need to respond?
  • Do their responses reveal some vulnerability or perhaps a “silly” side?

If there were enough positive signs and good feelings on the first date, you’ll likely find yourself making plans to see one another again.

Date #2

4. How would you describe your family…and your relationship with them?

Every child plays a unique role in a family. This question invites your date to tell you about his or hers, as well as share about the values, ideals, religious and cultural influences that were part of growing up. What you’re looking to see is if your date talks about his family with warmth or annoyance. If the latter, why is that?

5. What’s your relationship / marriage history?

If you want a serious relationship, the second date is not too early to talk a little about your histories.

You’re not asking for every single detail (nor should you share yours). Instead, you’re after an overview of their relationship experiences. Pay attention: Your date may reveal his or her attitude toward exes (positive or negative), as well as if she or he shares the responsibility for a relationship’s or marriage’s end – or puts it all on the partner. The conversation can also be a sneak peak into what they want in future relationships.

6. Are you looking for a monogamous relationship or do you prefer to date a variety of people?

I know it’s only the second date. And Yes, this is a big question. But if you’re serious about wanting a long-term relationship, it’s better to know your date’s intention sooner rather than later. He or she can’t give a wrong answer… but there is only one right answer for you. If it’s “looking for a monogamous relationship” and the chemistry is good, you’re probably going on to a third date.

Date #3

7. When it comes to a long-term relationship, what are your must-haves…as well as your must-not-haves?

Obviously this isn’t the only question or topic for the third date, but it’s the core one. This question presumes you know what your must-haves and must-not-haves are, of course, and are willing to share them honestly.

If you mention you’d like to be married and start a family within a year or so and your date freaks out, it’s a pretty clear sign that it isn’t in the cards for him or her – at least not on your timetable. It can be tough to distinguish someone’s ‘potential commit-ability” from their actual interest in a commitment… but that’s precisely what this question forces you to reckon with.

So there you have my 7 key questions to ask on the first 3 dates.

Before I sign off, I want to make good on my commitment to daters who want a serious relationship, but are no where near being able to ask these very direct questions.

First, let me assure you there is nothing wrong with where you are! Nor does a resistance to asking these questions mean you’re not meant to be in a relationship.

What it may mean is that you have some old belief systems about yourself and your fitness for a successful relationship that you may not even know you hold. In my experience, (personal and professional), these old beliefs need to be examined. Through that process, you will learn some truths about yourself – and the many positive traits you can bring to a relationship.

Some people can do this emotional work alone, but most find it more effective and efficient to work with a therapist or relationship coach. Eventually, doing it helps you become more clear and confident about what you want and need in a successful relationship – and how to go about achieving that goal.

In fact, I did exactly that to get unstuck and find the relationship of my dreams. And now my coaching practice helps people just like you do the same.

If you’re interested in learning more, please take advantage of my free 30-minute phone consultation.

Happy Dating!
Sue DeSanto, LCSW, is a relationship coach with a proven three-month program for helping people gain the clarity and confidence they need to be in a successful relationship. She offers interested singles a no-cost 30-minute strategy session to help them determine if relationship coaching is for them.

Am I Not Meant to Be in a Relationship

This is a question I hear fairly often, both in my therapy practice and from my relationship-coaching clients. When I ask people why they think that, this is some of what they say:

  • I’m afraid I’ll keep falling for the same type of person that’s not good for me
  • I don’t know where to start when it comes to dating in the Internet age
  • It must not be “meant to be” because it hasn’t happened yet
  • There are no good one’s left!

In my opinion, none of these explanations truly stand up to reason. There is not some Grand Poobah in the sky pulling the strings and deciding who gets to be – and who doesn’t get to be – in a long-term relationship. I hold the philosophy that if we really want a relationship, we can have one – no matter our gender, profession, age or looks.

The only thing stopping us is ourselves.

Some of you may react with, “Stopping myself? I feel like I twist myself inside out trying to figure out how to have a relationship.”

I believe you. What’s inhibiting you from achieving your goal is not a lack of effort. On a conscious level, you’re working your heart out. My hunch is that your inability to find that special someone is likely due to your unconscious belief system and behavior patterns that were established during your early life.

The experiences that lead to negative beliefs that ultimately inhibit our potential could have occurred when we were as young as 5, yet they remain alive and well in our unconscious mind. They are the hidden patterns of thought so ingrained in our unconscious, that we don’t even realize they are directing our life as an adult.

Believe me when I say, It’s not your fault. It’s like the saying goes, “We don’t know what we don’t know.” There is a way out, however. And that requires a true willingness to uncover what your core beliefs are, and the resolve to do whatever it takes to clear away the beliefs that stand in the way of your potential.

Therein lies the emotional, psychological – some may even say spiritual – work that is at the heart of relationship coaching, therapy, 12-step recovery, EMDR (Eye Movement Desensitization and Reprocessing), Emotional Freedom Technique (EFT) and any number of modalities aimed at making the unconscious… conscious.

Here are some unconscious beliefs that could impede relationship success:

  • I’m too fat (thin, ugly, smart) for someone to love me
  • My parents always said I was too sensitive (or too overbearing) to be in relationship
  • I believe a perfect relationship, like the ones described in fairy tales, is possible
  • My folks had a lousy relationship, and I’m afraid I’ll replicate their marriage
  • I’m afraid if I do get the relationship of my dreams, I’ll have nothing to strive for or complain about…and my whole life is about yearning for things I don’t feel I can get or deserve
  • I’m afraid I don’t have the capacity to love someone enough to be in a relationship

Because these beliefs are largely unconscious, they block our forward progress no matter how much effort we’re putting forth to achieve our goal. In fact, sometimes the harder we try consciously, the more our unconscious beliefs seem to dig in their heels and keep us stuck.

Most people, myself included, need the support of a trained and objective professional to do this type of emotional work.

It’s the foundation of relationship coaching as I practice it. My goal is to help you do the following:

  • Become aware of unconscious life patterns that keep you stuck
  • Help you understand why you may have those patterns
  • Support you in clearing those emotional patterns
  • Aid your efforts to get clear about what you want from a relationship, including establishing which needs are non-negotiable
  • Guide you toward meeting your relationship goals

Deciding to change can feel scary and difficult, and there can be a lot of internal resistance. As humans, it sometimes seems easier to stick with what we know rather than go “poking around” in our pasts or our psyches.

But being in relationship with others is what makes us fully human. They give us an opportunity to grow alongside someone through all of life’s challenges. They give us practice in negotiating for what we want – and making compromises when it’s for the good of the whole.

So while you may decide NOT to be in a relationship for any number of legitimate reasons, no one, in my opinion, is constitutionally incapable of being in one. All you have to do is be willing to do the work.

The choice is yours.

If you’d like to get started on changing your relationship story, here is a 10-minute meditation that can help.


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