Building Bridges

Issue # 41 of 43 

David LeClaire
By: David LeClaire

Intimate Inquiries

In issue #40, I talked about taking the time to understand what is important to you when evaluating a potential partner. After completing your list of Non-Negotiable items you should be in a much better position for the early "getting to know you" stage that comes with first dates.

We all know that it isn't easy to determine if our new special someone is a really good catch. We are all capable of being on our best behavior, especially at the onset of dating. Just as in a job interview, most people can appear to be a suitable candidate. Many times, simply asking questions and listening to someone's answers won't reveal their true character. One has to look deeper, for more consistency, to determine it they are honest and forthright.

As I suggested in earlier columns, it's helpful not to interview a new date, hitting them with a barrage of probing questions that may intimidate or scare them off. Using discretion and approaching the task at hand with elegance is much better. Taking your time, over a period of five to ten dates, to ask your own questions as well as the following suggested questions, will hopefully result in valuable insight into the person across the table from you.

It's important to remember, when listening to your date's stories, that this is their history and their version of what has happened to them, both in their lives and in their past relationships. Here is a list of some questions to ask to help get you started.

  • What is the most important thing in their lives, what is the least important?
    Maybe it's their kids, their job, their relationship, their hobbies, their health, or a myriad of other possibilities. This helps you understand how they will prioritize their time and energy, and understand where you may fit into the equation.

  • What are their personal and professional goals?
    What are they striving for in their life now, if towards anything? Are their goals so lofty that you feel they are unreasonable and they're trying to impress you? Are they so determined to accomplish things that it appears you may be just a fixture in their life if you get involved because making money or their career is really so important to them? If they have no goals at all, is it because they are bored, or boring?

  • What would your daily experience of life look like if you could choose it?
    Would they sleep in all day? Would they become a great chef, or would they always eat out? Would they have friends over all the time, or spend a lot of time alone? Would they have a different kind of work schedule, or change anything substantially? Remember, if it were to work out between you, could you or would you want to live their lifestyle?

  • What are their priorities with regard to relationships?
    This vague question is intended to be so open-ended that clearly there is no right or wrong answer. Maybe it's a healthy, active sex life. Maybe it's becoming friends first. Maybe they want a balance, time with their friends, alone, and time together. Again, this is just a possible clue in how they will want to pursue being in a relationship with you.

  • What lessons have they learned from different partners they've been involved with?
    Another related question is "What have they learned about themselves in relationships?" This doesn't mean specifically to one partner they've had, but overall, as in what are the things that stand out in their mind that they know won't work for them and what have they learned they really need to be happy and be able to weather storms? These questions will tell you much about their maturity level and ability to see even broken relationships as learning experiences. Hopefully they can articulate some benefits out of their past endeavors, and are moving closer to understandin themselves and what they need as a result of their past. If not, that's a big warning sign to steer clear of them.

  • How did your last relationship start? Was it passionate and then it quickly dwindled, or did it grow slowly? How did it progress?
    It really doesn't matter what the answer is in the sense that there isn't a right and wrong way to start off a relationship. But it may cue you in to a possible pattern or tendency of Lover X. How did they feel about the way the last relationship developed? If they thought it started off too fast and became too serious too soon, it may help you understand why they are being cautious and taking the slow, back roads when it comes to you. Or vice versa of course!

  • Why did your last relationship not work out?
    (Look for whether or not they take any responsibility for their actions, for their role in a terminated relationship.) If it's all the other persons fault, you can bet it'll all be your fault when problems arise between you down the road.

  • What would you say your biggest fear is when it comes to relationships?
    This should highlight what has gone wrong for them in the past, the things you want to know that are areas that they'll be watching for or are very sensitive about. Maybe they'll respond with something like "Criticism. It seems my partners always are finding what is wrong with me, instead of focusing in on what they like. I really hate that, and I'm afraid that after the newness wears off, that'll happen again." If you're really into digging, you might want to inquire what things their last partner criticized them for, giving you a tip into a possible scenario that could unfold down the road with you as well.

  • From past experiences, what do you think your most significant challenge or weakness is with respect to being in a long-term relationship?
    Let's say they respond with something like "Being content with one person sexually, forever. " That is a much different response than "Controlling my anger," or "Working too much." Either answer may lead to a what may lie ahead for the both of you. Remember, they're not going to tell you how horrible of a person they are, so you may need to look a little farther than their first answer to this question. Wouldn't it be nice if you could hear what their last lover would say about them in regards to that same question?

  • Is there anything anyone has ever done to you that you've never been able to forgive them for?
    The answer to this could tell you if they really have to search for something, or if they hold a lot of grudges. They may end up telling you about an incident that never was healed in their life that could be valuable and worthwhile to know. There could be some unhealed wounds that, although don't have anything to do with you, may be something you'll eventually have to deal with. Some people say "why worry about all of these things ahead of time - why not cross that bridge when you get to it?" I say, why not be more proactive in getting to know where you may be heading with someone BEFORE you invest lots of time and emotion into them. I'm advocating making informed decisions about a very important choice in your life. Take your time in discovering who this mystery person is, that's part of the fun. Whatever you do, don't pull out this list, and announce, today's question is......

There is little doubt, that for those of you looking for that special someone, the highs that accompany any new relationship can be intoxicating. Enjoy this time but keep in mind, however, that the chances of your relationship becoming a long term, and successful one, will be determined by your ability to communicate openly and honestly with your potential partner. Ask your questions and listen carefully to all their answers.

Have fun and Good Luck!

David LeClaire has spent much of his time teaching at community college and private school, and lead communications training for Fortune 500 companies. Now a popular and active Seattle area sommelier, this graduate of Central Michigan University led seminars for a wide variety of organizations. LeClaire is the author of "Bridges To A Passionate Partnership." He can be reached at

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Text © 1998, David LeClaire. Part of the original Sideroad.
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