The Dating – Having a Way Cool Time

Presumably you’ve planned your dating carefully and are fully prepared. (If not, flip to Chapters 11 through 13 for a refresher course.) At this point, I’m confident you not only know where you’re going, how to get there, and about how much it’ll cost, but you’re dressed appropriately, and you’ve fully factored your date into the equation. You’ve selected a destination you both will like and haven’t decided that now would be a good time to start smoking, wearing fur, or pinning a campaign button to your lapel.

Now you’re all set to have a good time. This chapter tells you how to make the most of your date, how to deal with the unexpected catastrophes that may creep up, and how to end the evening gracefully.

Enjoying Yourself

It doesn’t have to be the Fourth of July for you to have a great time on your first date. The sky doesn’t need to erupt in fireworks for you to consider your date a winner. What does need to happen is that you create an environment that allows both you and your date to relax a little, let your hair down, get to know one another, and have fun. The basics of enjoying yourself are fairly straightforward.

Don’t sweat it — it’s pretty hard to really screw things up. Besides, it’s only one date. With a bit of pre-planning on your part — which is, essentially, what all the earlier chapters have been about — this date can be a really cool one.
Pace yourself. A date has a beginning, a middle, and an end. You’re not on the clock. Your date doesn’t have to love you in the first five minutes or it’s the ejector seat. You don’t have to love your date instantly either. Keep reminding yourself what a date is really all about: getting to know one another. Relax. Enjoy yourself. And take it easy.

Making the Most of the Place You Picked

Food is part of a time-honored traditional date activity, so figuring out how you can make eating out a delicious experience is time well-spent since eating “in” is for later on — after you get to know each other.

Order food you eat with a fork

Forget about sandwiches (unless that’s all there is — in that case, the fewer ingredients, the better). Food you lift with your hands can easily fall from your hands. High-rise sandwiches are notorious for collapsing on the way up to your mouth. Stringy pizza cheese dangles from your lips like you just swallowed twine, sushi is rarely served in petite bite-sized portions, and tacos spill.

Don’t drink

I know, I’m going to lose a lot of you here — if you’re nervous you might be trying to relax yourself. But Miller Time can become mildew time before you know it. Be very careful about alcohol. If you’ve ever had a problem with alcohol, unforgettably — don’t drink. I can already hear you muttering, “Hey, a drink or two will relax me. I can handle it,” but it’s you that I’m talking to here. Moderation when you’re nervous is difficult to achieve, so err on the side of caution here and believe that alcohol on a first date is dangerous for several reasons.


Okay — so I’ve put alcohol off-limits, but it’s okay to indulge in dessert calories. Most men are much more comfortable with women who eat reasonably rather than the “Oh, I’ll just have a small salad with the dressing on the side” syndrome. (Surveys show that women put much more pressure on themselves to have a “perfect” body than men ever put on them.)

It’s okay to share a dessert. First of all, you’ll find out if he works and plays well with others. Secondly, it sends a loud and clear message that you’re not anorexic or obsessed with your weight. Watching your waistline is one thing, entering a convent is another. Eating is a sensual, pleasurable experience that’s meant to be savored.

I’m not saying you should throw calories to the wind and use date night as an excuse to imitate Miss Piggy, but enjoying yourself means letting go enough to enjoy your date, the conversation, the location, the colors, the smells, the sights, the sounds, and the meal — the whole enchilada or creme brulée.

Tip well

I’m talking 20 percent. At least. Generosity is attractive. Trust me, the miser never gets the girl. He may keep a few extra dollars, but a person who is tight with money is unlikely to be generous with time or self.

Mind your manners

Good manners count. Make no mistake about it. Nothing is a bigger turn-off than seeing food churning round and round inside your date’s open mouth. Ugh. Or being rude to waiters, talking too loudly, picking up peas with a knife. and sliding them down your throat. Think Jane Austen or Masterpiece Theater or that guy who pulls up in his Rolls and asks, “I say, have you any Grey Poupon?” You want to be prim and very proper. At the very least, do these things.

Movies or plays

This dating venue is a double-edged sword. On one side, you’re creating a “shared experience.” Good for bonding. One of the stepping stones of intimacy. On the other side, most of your date will be spent in the dark staring not at each other. Not the ideal way to get to know somebody. To make the most of a movie or play, be open to discussing it afterward. You can talk about the plot, the casting decisions, the money it cost to make it, other movies you’ve seen that you like better, childhood memories this movie evokes — anything. If it was horrible, you can talk — and laugh — about that as well.

I know I already mentioned this in Chapter 10, but it’s worth checking to make sure that your date approves your choice. Surprises will be more effective once you are more certain of each other’s tastes!


A concert lets you relate to each other while the music plays, or in the midst of a break. So relate already: Bob back and forth together with the beat, scream in each other’s ears to be heard over the noise, and, when your ears are ringing
afterward and you can’t hear anything anyway, just smile dopily at one another.

Besides, if you aren’t having a good time, you can leave a concert mid-stream without wondering all night if you missed the really good part. Simply buy the CD.

Sporting events

It’s often much more fun attending a live sporting event than watching it on TV. Even if you’re not into football, you can get into nachos and peanuts. It’s outdoors (usually) and in daylight, and you can even paint your face the color of your favorite team.

A Word about Silence

Everybody worries about not having anything to say, but if you can remind yourself that you’re the “you” expert and you’re curious about your date, then you’ll be able to maintain the conversational flow without panicking over silences. In general, you want to reveal who you are without confessing every flaw, being sexy without being sexual, funny and light without being desperate for a laugh. If you’re not sure what to talk about once you get there.

Fielding the Curve Balls

A curve ball (or two or twenty) is waiting for you on this first date. You can take that to the Dating Bank. No matter how well you prepare, something may go amiss — or at least, not according to your Pentagon-perfect plan. It’s Murphy’s Law of Dating. The trick is to prepare for the worst and then relax and field whatever may come your way.

Surviving dating’s most embarrassing moments

One of my best friends remembers her first big high school dance as bittersweet. It was a formal affair (as they were in those days), the guy she’d had a crush on all year had asked her to go, and her dress was to-die-for. That’s the sweet part. Her bitter pill was waking up the morning of the dance to find a giant pimple perched on the tip of her nose like Mount St. Helens. The more she fussed with it all day, the worse it got. That evening, as the doorbell rang, my friend was squirreled away in the bathroom frantically powdering the tip of her nose — which by now rivaled Bozo the Clown’s. A bona fide disaster.

She left for the dance with one white-gloved hand hovering over the front of her face. Perhaps, she consoled herself, her date wouldn’t notice. He did. After all, her uncomfortable behavior was as plain as the nose on her face.

Ending the Date Gracefully

At first glance, it would seem easy to know when a date is over. The empty dishes have been cleared off your table, the check is paid, the theater lights are up, or the sun has risen. There are definitely markers. But a date is an emotional event. What’s an empty restaurant and five glaring waiters when this could be true love? Plus, if things are going well, you’re also battling your biology.

When you’re in the throes of infatuation, a chemical in your brain called phenylethylamine (PEA) causes those tingly feelings of euphoria. Other neurochemicals, namely norepinephrine and dopamine, may also play a part in your “lover’s high.” These natural “uppers” are what cause lovers to stay awake all night gazing into each other’s eyes or talking into the wee hours of the morning. Sadly, or perhaps thankfully, this chemically induced elation fades. Your brain can’t stay in a revved-up state forever!