Having Fun on First Dates---Are You Serious?

"Dating shouldn't be work---it should be fun!"
(Advertisement for meetoverdrinks.com)


I know nothing about the new matchmaking service, meetoverdrinks.com, but I do like the tagline they use in their print advertising. Yes, dating should be fun.

However, if you talk to as many mid-life singles as I do, you know that, for many of them, dating is anything but fun. I regularly hear stories about first-dates-from-hell: men who haven't bathed in a week; women who go into excruciating detail about each of their eight past lives; people who get up to use the restroom and never return (sometimes sticking the other person with the check); people who are ten years older and sixty pounds heavier than in the pictures posted on the dating site.

And let's not forget the mental-checklist people: the ones who have to know within the first ten minutes everything about your marital, sexual, and employment histories, your drinking habits, your political inclinations, and, of course, your assets, prospects, and disposable income.

I don't doubt the truth of such stories and I know that they're not uncommon. In fact, with so many people meeting for the first time after a couple of brief e-mail exchanges, the opportunities for mismatches are endless. But, no matter how obnoxious, inquisitive, or just plain crazy the other person turns out to be, you can still actually have fun---or at the very least an interesting experience---if you have the right attitudes.

Perhaps the most basic attitude is that you're there to enjoy yourself and, perhaps, learn something. You're not there (necessarily) to meet the love of your life. You're not there to conduct a job interview or a legal deposition. You're not there to ferret out every possible weakness or failing in the person sitting across the table from you. You're there simply to spend some time with another human being.

Not all human beings, of course, are people you'd want to see again. But even someone who's an extreme mismatch in a romantic sense may have qualities that you might find interesting, so long as you don't think of him or her solely as a potential lover. Years ago, when I was using newspaper personal ads to meet women, I met some who were clearly "wrong" for me, but whose conversation or personality I still enjoyed. In some of those cases we continued the relationship on a purely platonic level. In other cases I never saw them again. But I don't recall ever regretting the time I spent with someone on a first date.

If you've got a positive attitude, no experience, no interaction, is totally wasted. You'll learn something about yourself, about the other person, about the opposite sex, and maybe about life in general.

Of course, with some people a little bit goes a long way; you can learn all you need in thirty minutes or less. Fine. That's why first dates should always be low-key, low-cost get-togethers at coffee shops or other informal places, places that are easy to extricate yourself from if need be (or to linger at if things are going well).

Another good attitude is that there's nothing wrong with letting things unfold naturally. Except in cases where there is either no attraction whatsoever or an instant, head-over-heels chemistry, people shouldn't try to decide on the spot whether they might have a future together. I think it's that need to nail things down that leads to the "checklist" mentality I mentioned. People like that somehow feel that, by the time the date is over, the other person has to be either a Yes or a No. Well, people are complex creatures who don't always reveal themselves to full advantage in thirty to sixty minutes. And people definitely aren't at their best when the other person is peppering them with nosy, or even hostile, questions. There's nothing wrong with labeling someone a Maybe, and holding off on any decisions about future meetings until you've had time to reflect on the initial experience.

And, if all else fails, your attitude should be that bad dates produce good stories. When you do eventually meet the person who rocks your world, the two of you will get a lot of laughs recounting the absurdities and the sheer horrors of those dates-from-hell. And you will have developed some attitudes and practices that will serve your relationship well in the years ahead.