Savvy Dating 101: How to Enjoy First Dates

Ever noticed how dating, American style, often feels like a job interview? Two people sit across from one another at a predetermined site and ask all manner of questions ranging from, “What is your pet’s name” to, “Where do you think this relationship is going?”

The pet thing? Cute. Relationship questions? Please don’t go there. There is no relationship yet. This is a first date where you decide if another date is even an option.

Let’s be clear. First dates are something we do to find out if we want to have a second date. No one needs to be talking about “the future” this early on. While it is true that serious questions must be asked at some point, the first date is NOT the time to probe into questions about a possible commitment. Asking questions about where the relationship is going right now is a sure-fire way to give your date an excuse to do the famous MAGIC DISAPPEARING ACT!!

Now you see him; Now you don’t. Poof! It’s a remarkable act when you think about it. The irony, however, is that we often fail to realize how or why our dates suddenly disappeared!

In any event, a first date has been secured. During the course of the date, we proceed diligently onward to create (mostly inaccurate) assessments in our minds about the person we are sitting across from, usually within one hour or less. Nevertheless, if we believe most of our questions have been answered in a satisfactory manner, we grant the opportunity for a second date. Yes indeed, another “interview” has been secured.

Mr. Extreme Interviewer Guy


It is no wonder that so many men and women dread dating. Clearly, the ‘date as interview’ paradigm purports judgment, which does not and cannot lend itself to feelings of intimacy and pleasure…. which is what a date is supposed to do! Yes indeed, dating should actually be fun.

You see, the date-as-interview technique is a real bummer for the person being questioned. For example, I know a woman whose date maintained that he could not proceed with the relationship unless the following questions were answered to his satisfaction. Amazing story, but true, nonetheless. The following were his questions:

  1. What is your religious affiliation?
  2. What are your politics?
  3. What is your financial status?

He was Mr. Extreme Interviewer Guy, the one with an inflexible checklist who, by the way, will never find the perfect woman because the perfect woman does not exist…. not does “the perfect man.” Who knew?

Rumor has it, Interviewer Guy didn’t get the memo, the one that states: No One is Perfect, Least of All You. Needless to say, Extreme Interviewer Man totally flunked Savvy Dating 101. He a kill joy and he doesn’t even know it.

So, this nice lady went home thoroughly depressed, poured herself a glass of wine (probably several) and called her ex-boyfriend who is still available, but whom she doesn’t even like anymore.


Patience is a Virtue

Dating needn’t be a miserable experience. To be successful in dating, men and women really have to ease up a little and really learn how to practice some patience. Obviously, we don’t want to welcome trouble by dating any insensitive person who comes along. Rather, once we’ve decided to date someone we think is worthwhile, we must give the dating experience a chance to grow by allowing some time and space for the person we are curious about to reveal themselves, at a reasonable pace. It is important that dating couples learn to let go of preconceived notions about the perfect date. In short, we must let go of our rigid expectations if we truly want to date successfully.

Another misconception about dating is that we must only date someone we are pretty sure we can eventually marry. “Non,” as the French would say. At what point during dinner do we determine such a thing? First, we must learn to lighten up and have fun with our dates, as if we are just friends. Simple concept, but it works in that changing your mindset helps remove much of the sexual pressure dating couples may feel on first dates. Besides, there is plenty of time down the road, on other dates, to determine whether our date may one day become our lover or our spouse.

Nothing But the Truth?

When asked probing questions, most people try to give “correct” answers to questions, but not necessarily truthful answers. In fact, most people will give answers they think are “right” answers. Just because someone asks a direct question doesn’t mean they’re going to get an honest answer. Thus, asking interview questions defeats the purpose of getting to know the real person, when you stop and think about it.

In fact, the few brave souls who are willing to reveal “the whole truth and nothing but the truth” on first dates, also happen to be the same individuals who almost never get a second date. As Jack Nicholson said in A Few Good Men, “You can’t handle the truth.”

After all, what person in their right mind really wants to know about their date’s psychotherapy sessions… or how much it hurt when they passed a kidney stone… or why they think their ex is a psychopath, all before you’ve had a chance to finish your salad? On first dates, too much information is not a good thing. All the experts say so. Believe them. They know what they’re talking about.

Three Easy Rules

Nevertheless, we still have to communicate. Rest assured, we stand a fighting chance at dating well by realizing three things. They are as follows:

  • Ask interesting and fun questions instead of interview questions: Questions should be interesting and intriguing; the kind that cause people to ponder a bit, to feel happier somehow, and also to feel a bit wiser. Good questions draw our dates toward us and make them want to open up even more.
  • Have patience: Patience is a virtue. In short, stop trying to control the future. After all, there is no way to know for sure, right now, if this man or woman sitting across from you wants to love you forever. In the beginning stages of dating, we must learn the art of leaning into the process, that is to say, learning to relax and actually enjoy someone’s company just as you would a friend, knowing that, in time, a person’s actions will reveal all we need to know about their true character.
  • Inject easy humor into an already awkward situation: Humor helps, but you don’t want to go overboard. Your date also needs to know you can take serious things seriously.

Good Questions Lead to Great Conversation

It’s not a bad idea to take a cue from the Zen Masters, by living in the present. Yes, Americans are fond of instant gratification and we want the future now, but love doesn’t work that way. Anything worth having is worth waiting for. Romance must have time to flourish like a beautiful, healthy plant. Having said that, we still need to figure out some things about the person we have chosen to date.

A good way to do just that is by asking unusual and interesting questions, not job interview questions. E-Harmony, a respected online dating site, is smart about suggesting good questions for first dates. Here are some of them:

  • What’s one thing about you that would surprise me?
  • Do you have a nickname? What’s the story behind it?
  • What is your favorite movie of all time?
  • Where do you feel most relaxed?
  • What would you do if the sky is the limit?

If you ask good questions, you’re going to get revealing answers. That’s the way it works. If your conversation leads you to believe your date really isn’t for you at all, that’s fine. There are other fish in the sea. On the other hand, if your communication has revealed that you and your date have a lot in common, then you have a decision to make about whether a second date in order? If you’re not sure, sleep on it. If you believe there may be a chance for something special, don’t wait too long to make up your mind. You don’t want a good one to get away.

It is important that we stop projecting into the future or maintaining inflexible expectations about how our dates are supposed to behave. That being said, if your date isn’t showing proper respect, manners, or basic decency, then you have every right to walk away or call them out on their behavior.

Pleasurable dating must unfold naturally and proceed in stages if we are to allow romance a chance to thrive. At first, keep the conversation on the light side. Any talk of sex, finances, and politics can and should wait. There really is no rush to dig into these topics on a first date. After all, only time can allow a romantic narrative to unfold into something marvelous, maybe even into something as wonderful as lasting love.

Happy Dating…. Yves

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