Low-Stakes First Dates

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.


15 thoughts on “Low-Stakes First Dates

  1. These sound great — very practical, and I like your writing style.
    Say, I’m going to check out this neat used book store a friend told me about. I was thinking Saturday afternoon. You want to come with me and maybe get coffee after?
    Take care,

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  3. Very droll, and very well considered advice.

    Especially not engaging in protracted flirting.

    Although I would note that shy people– and movie fanatics– sometimes like going to movies on a first date. Shy people since it’s a great opportunity to sit companionably for a couple hours without *having* to talk the whole time– and movie fanatics so they can suss out the other person’s all-important movie theater etiquette. 😉

  4. Excellent advice, and well said.
    You know how long it’s been since I’ve had a first date. My opinion is that getting to know someone slowly is wise. Then, by the time you raise the stakes, you know you’re interested for sure.

  5. Completely disagree about the movies being a bad first date. GREAT first date. With online dating, you never really know how attracted you are going to be to the person once you actually meet them. Going to the movies is a great way to sort of dip your foot in first. After the movie though, you should ALWAYS grab a drink or coffee or something, even if you are not attracted to the person because otherwise that would be incredibly rude. The movie provides a good conversation starter…and who knows….maybe with conversation, you might start to be more attracted to the person. If after all that, it’s a no-go….fine..movie…conversation…all good. If you go into a date with someone that you immediately realize you are not attracted to in person, conversation will be awkward because it will be tainted with disappointment. And if you are insanely attracted to the person, it could also be helpful to have that movie as an adjustment period, so thay you are not too drooly. 🙂

    • JJ: Thanks for reading, and for commenting!

      Two key features of a low-stakes approach:
      * Spend your first date giving yourself and your date opportunities to decide whether you want to proceed
      * Make and communicate an honest yes/no decision about whether to proceed

      There’s nothing inherently wrong with going out to a movie and getting a drink afterward. I’m offering an alternative to people who’ve tried that and found that it doesn’t work for them. If it works for you—hey, wanna go to a movie? 🙂

  6. Hey, great article Benji. Especially cause it’s stuff that I already believe about dating. It was nice to see it written so concisely. (I followed the link on the “how to be weird” post.) So now that I’m sure about what to do on first dates, can you find me some nice men in Seattle?! 🙂

  7. i can’t imagine myself going home with someone on the first date. not because i consider myself a prude (probably as far from that as you can get) but due to my anatomy it just seems needlessly risky for a potentially mediocre outcome. so it’d never occur to me that someone would need to be told not to plan for that. but maybe they do? it also seems risky in terms of drama… you never know if that superhot person who’s ready to come home with you is also a psychostalker =P

    i do strongly disagree with the idea that you should avoid a novel activity with a new person, though. i assume by default that a random person from a dating website is probably not going to be that great. if they turn out to be great, i’m pleasantly surprised, but i figure that there’s a much higher chance that this will be a decent conversation with someone that i’ll never see again.

    but if a date causes me to do something that i might not otherwise have done, that’s adding a lot of value. even if it turns out that i have no interest in the person, i now have a new and interesting experience under my belt. if it turns out i like it, i could later try it again with someone who i am really into.

    i also generally consider people a good influence if they introduce me to something unique and interesting, even if i’m not attracted to them. so i’d think more highly of someone if they did that vs. if we just went to a coffeeshop which i could do whenever.

    i’m an idealist, but i think that if someone is a person i’d enjoy dating, we’ll be having a good time regardless of whether we are doing something that i end up not enjoying or whether we’re at a coffeeshop. company makes all the difference.

  8. Good article.

    Another great idea (recently experienced): find a coffee shop or bookstore with board games or similar entertainment, have a cup of coffee, chat, and play a game. It’s interactive and engaging. Had a really fun first date recently that involved a new (and fabulous) game that neither of us had played.

    Heck, I even bought the game afterwards!

  9. I prefer the end of date rule that you ask for the next date at the end of the first date. “I had a great time. Are you free [in a couple days].” No one tells west coast guys about this. Cuts post date neuroticness and lets the person know in clear terms — you are worth seeing again.

  10. Very nicely written. I recently had my second date and having my third tonight which is actually to see a movie although a sleep over is happening too. Your article has reinforced my opinions of my first two dates and I now feel a lot more confident that they really did go as well as I had thought they did.

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