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!

Testimonial 4

I have worked with Sue De Santo and I am so grateful for her expertise, wisdom, guidance, and encouragement. Through her Relationship Coaching Program, Sue expertly led me through exercises and discussions to explore who I was, my past relationship experience and most importantly where I wanted to go and what kind of relationship I was looking for. I feel like I have blossomed under her supervision which has allowed me to become the person I want to be and to find the healthy, enriching and satisfying relationship that I wanted and deserved. She encouraged me to partake of the “dating buffet” and I did and got great results and had a lot of fun doing it. Thank you Sue!

—BS, Chicago

Keep the 80/20 Rule for Relationships in Mind This Valentine’s Day!

valentine's day advice

It’s that time of year again! Heart-shaped candies are filling the aisles, red and pink decor is filling up every available space, and love songs are in the air. That can only mean one thing – Valentine’s Day is almost here!

Whether you’re in a relationship or not, Valentine’s Day is a holiday that can cause a lot of joy – and also a lot of stress. However, there’s another way to look at “the day of love.” We can use this as the perfect opportunity to reflect on our current relationships. Whether you’re single or in a loving, committed relationship, it’s always important to reflect on behaviors and patterns that may be holding you back or causing issues. That’s where the 80/20 rule for relationships comes into play.

The 80/20 Rule for Relationships

If you’ve never heard of the 80/20 rule, it’s the theory that you only get 80 percent of what you actually want out of a relationship. Even if that 80 percent is really amazing, we still search for that missing 20 percent. And the search for that missing 20 percent of what you want out of a partner is what causes people to cheat.

Why do we feel that the 80 percent isn’t good enough? Why are they constantly searching for that missing piece? Many place the blame on their partner because that’s the easy explanation. They aren’t giving you everything you want and need in your relationship, so of course it’s their fault. However, I beg to differ. I have my own take on the 80/20 rule.

80 percent of the issues we have with others are actually our own internal struggles. The other 20 percent are issues within the relationship. Oftentimes, we project our own judgments, fears, and ideas onto others. We go into a relationship expecting to get something out of it, and when we don’t get what we want or need, it’s hard to feel completely settled or happy.

Look Within This Valentine’s Day

Valentine’s Day is all about showing others how much we love them. But in order to do that, we must first start with loving ourselves. This Valentine’s Day, I challenge you to take a look within to identify patterns that are causing challenges in your relationships. In order to do this, you have to take a close look at your own judgments, assumptions, and expectations. The next time you’re on a date and find yourself annoyed with something your partner is doing, take a step back to reflect on the judgments you’re making. Ask yourself if what they are doing is really that bad, or if it’s your own internal struggles that are warping the way you’re looking at the situation. Taking a moment to work through it before rushing to irritation will help you handle anything your date is doing with ease and maybe even a sense of humor.

Remember that YOU have the power to work on the 80 percent of your relationship, while the 20 percent is a joint effort between yourself and your partner. In order to build a relationship that lasts, it’s important to work through you own personal issues to be able to build something real with your partner.

If you’re not sure how to go about working through that 80 percent, you might want to consider relationship coaching. Together, we can figure out the difference between your own needs vs. what you need and want out of a relationship. Contact me today to get in touch and learn more about my relationship coaching program!

Tips for getting clear about finding your true love NOW.

Sign up and take our free Love Quiz!