Picture this: you take a thousand dollars out of the bank and go to Las Vegas. You put on your finest clothes and hit the nearest casino. You buy a $1000 chip and stride over to the roulette wheel, looking fabulous and confident. You put the thousand dollar chip on your lucky number, and the wheel spins…and you spend the rest of the weekend alone in your hotel room, wondering why bad things have to happen to you.

That’s how lots of first dates feel: with everything riding on the outcome of this one big chance, romance and excitement quickly give way to confusion and dejection. Sound familiar?

Don’t bet everything on the first date: lower the stakes.

Low-Stakes First Dates: The Basics

I was introduced to the idea of low-stakes first dates by — who else? — a woman with whom I was about to go on a first date. I’d started meeting women through dating websites, often exchanging boastful, flirty email for weeks before one of us finally felt confident enough to ask the other out. What happened then was usually a rushed and awkward first date, and you could almost see our expectations hanging in the air like cartoon thought balloons. One day I sent off a particularly over-the-top flirtation, and got this response: “Hey, cool your jets. No need to build things up before we meet. We might not even like each other. Want to go get a beer tonight at 7?” I learned a lot about low-stakes dating on our first (and only) date.

Have the first date as soon as you know you want to have one.

Don’t spend six months trading witty e-mail banter. Once it’s clear that this is someone you want to know better, make a date.

Flattery feels good, but it raises the stakes.

As much fun as it is to flirt, it does make it harder to keep it low-key.

Good First Dates

A good first date is a shared experience of something that leaves room for casual conversation and offers opportunities to tell stories and articulate thoughts, but doesn’t last too long. How about lunch?The date needs to have a definite end: some natural and obvious point at which you two will go your separate ways. If you have dinner together, linger over dessert instead of going onward to a bar. Arrange to meet at the restaurant, rather than being picked up — and therefore dropped off — at home.

The reason the date needs to have an end is so that you don’t end up having sex. Don’t even make out, and don’t go home together, even just for one drink. If you’re really into this person, a solid goodnight kiss says enough.

Bad First Dates

Going to a party where your date won’t know anyone

You’ll either snub your friends, snub your date, or spend your time managing your date’s experience. Or maybe all of your friends will absolutely love or totally hate your date… which raises the stakes.

Situations that prevent you from speaking or looking at each other

Movies and theater don’t make good first dates, since sitting wordlessly in the dark for two hours is a lousy way to get to know someone.

Situations that can’t gracefully be adjusted or ended once they start

A four-hour sunset cruise is a great date… until you get seasick, or your date casually makes a racist remark.

Stuff you’ve never done that they absolutely love (or vice versa)

This is a tricky one, for a few reasons. There’s a good chance of awkwardness if one of you is a fish out of water. Even if you have fun, you’ll be dealing with the novelty of the experience instead of, you know, being on a date. Save the fun-but-risky dates for later.

The Next Day: Communicate Clearly

You don’t have to sit around waiting for the other person to call you, but do sleep on it before making that call yourself. Talk to a friend to find out how you really feel about the date.

How DO you feel about the date? What did you like? What wasn’t so great? What would you want more of, and what would you want to avoid in the future? Noticing how you feel about these things will deepen your understanding of what you (a) really want, (b) gotta have, and (c) won’t tolerate. That kind of self-knowledge is a key to romantic happiness.

As you reflect on these things, you may be tempted to downplay the downsides by focusing on your date’s redeeming qualities, but that’s not how it works: some flaws are dealbreakers, no matter what. The reverse is also true: a good date needs to have qualities you really like! An absence of huge defects should not be your standard of excellence.

My lovely and brilliant pal Damiana Merryweather is an expert on first dates, and she has this to say on the subject: “Don’t compromise on anything more important than pizza toppings. ‘He did tell a racist joke, but he held the door and paid for dinner.’ ‘He wants to ban abortion and thinks wives shouldn’t work outside the home. But he was so cute! We like the same authors!’ Just move on. There’s somebody out there who’s just right. Don’t waste your time with somebody who is just sorta okay.

If you’re into it, say so. Say it simply and leave room for — ASK for! — your date’s opinion on the matter. Remember, the stakes are low. If your date isn’t interested in you, this is a great time to find out: leave room for that possibility while being clear about your own interest.

In the unlikely event that your date isn’t interested in seeing you again: hey, no big deal. Congratulate yourself for having kept it low-key. When you’re ready, make a date with one of the other several billion people out there.

If you’re not into it, say so kindly and unambiguously. Don’t specify a particular reason for not being into it. As a near-stranger, your opinions will bear a lot of weight, so be charitable to your fellow human and just say that you didn’t feel that certain romantic spark that you’re looking for. Good luck and best wishes, sincerely, period. Vague mild disappointment sure beats specific intense disappointment. This is your last chance to disappoint gracefully — while the stakes are still low.

If you’re both interested, make a second date!

The Second Date: First Date Part Two

The second date is really just an extension of the first date. You’re still just getting to know each other — you haven’t even seen each other naked (right?).

Good second dates

As before: a good date is a shared experience of something fun that leaves room for casual conversation and offers opportunities to tell stories and articulate thoughts — maybe something you talked about during the first date. One exception to the “No movies” rule from the list of bad first dates: You might consider going to a well-reviewed movie that you both really want to see. NO ART FILMS — think in terms of comedies starring actors you both love. If you pick one that’s been playing for a few weeks, you might even have a little privacy in the theater. I’m just saying.

Bad second dates

The list of bad first dates still applies (aside from the movie exception above). Also, sex.

Third dates and beyond…

Hey, slow down. I’m only ready to talk about first dates.

But if you want some general advice: take it slow, be mindful of your feelings, and think about whether you’re getting what you want and comfortable with what you’re doing. You’ve got this dating thing under control.

How to Get Good at First Dates

Have more of them. I like http://www.okcupid.com.

Love,

Benjy