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.


The manager’s job hasn’t changed.

One of my [awesome, brilliant] coworkers shared this article with our team:


The article reflects on the pop-neuropsych trend in management literature (How We Decide; Predictably Irrational) and its unsettling effect on a 7 Habits/Who Moved My Cheese world. This bit stood out for me:

[…] Instead of a management philosophy centered around the manager as the play-caller, assigning tasks and motivating people to carry them out, we are told by the neuroscientists that the new management job is one of facilitating more of a customized, do-it-yourself process centered around each newly-energized employee, one centered on questions (often leading) rather than direction.

Most business literature focuses on methods that managers can use to solve their problems, and it’s tempting to believe that the manager’s job is to become as skilled as possible in using the best of those methods to get people to do their jobs. But the methods aren’t the place to begin; the first challenge for a manager is to define the right problems. High-quality problems usually follow a simple pattern, like:

What must we do to fulfill our purpose?
What can we use to do it?
What are the circumstances under which we’re working?
Who are ‘we’, anyway?

Once the problem is defined, then it makes sense—and is much easier—to structure and implement the team’s jobs in a way that results in a solution. There are lots of ways to structure different jobs to get the same work done:

  • it might be delegated into a senior staff member’s responsibilities
  • a mid-level team member might do it under the manager’s supervision
  • a senior staffer might be responsible for coaching junior employees through it
  • or the manager might do that work herself

Calling the plays, assigning tasks, motivating, facilitating, customizing, coaching, subtly manipulating, setting direction… these aren’t the management job. The management job is still the same as it ever was:

managers design jobs, starting with their own.


P.S. See also: http://monkeybagel.com/pumas.html

“Nice camera!”

I like people a lot, and I shoot almost nothing but portraits and candids, mostly at events like parties and nightclubs. People often come up to me and say “Nice camera!”

I used to think they were actually talking about the camera, and I’d smile and say “Thanks! I like it,” or if I was REALLY drunk I’d tell them the total cost of the body, lens, haze filter, flash, and memory card, and that would end the conversation without much reason for either of us to like the other.

Now, when I hear “Nice camera!”, I take it as:

1. a vaguely well-meaning compliment
2. an expression of interest: in photography, in being photographed, or in me personally

So I thank them for the compliment and sometimes that’s that. But if I’m interested in continuing the conversation, I reply with a question. Some examples:

“Thank you! Are you into photography?”

Sometimes they are; sometimes not. What’s really gratifying is talking to the people who love to take snapshots and are looking for just a little bit of permission from an “expert” to begin thinking of themselves as photographers. For those folks who next ask “What kind of camera should I buy?”, sometimes I go through the whole conversation: what do you have now? what do you want to do with it? are you likely to carry a big camera around? But what I often say now is:

“Buy the newest Canon Rebel you can afford and a 50mm f1.8 lens. Set it to “A”, set the aperture to f/2, and take pictures of your friends without flash. Put the good pictures on Facebook or Flickr. If you haven’t used it after 6 months, sell it.”

In any case, asking about their interest in photography is a chance to get them talking about themselves, which is a good way to make friends.

“Thank you! Can I take your picture?”

Sometimes that’s all they wanted in the first place; in that case I do it and then tell them to find me on Facebook (*cough* http://facebook.com/benjyfeen *cough*). I’ve met a lot of people that way. A variation on that response is “Thank you! Hey, that’s a cute (tattoo | dog | ironic T-shirt | bunch of friends). Can I take a picture of it?” This is different from just asking to take their picture; it’s a compliment on their taste, rather than their looks, and it’s an opportunity to have a more general conversation.

I enjoy connecting with most people, so it’s nice that photography offers me that opportunity. When I’m not in the mood to connect with someone, I like knowing how to bow out gracefully. And hey—sometimes they just think it’s a nice camera.

In brief: don’t buy a cheap zoom lens.

When you’re learning a craft, the best tool to use is the one that shows you the limits of your ability. It’s the eight-inch chef’s knife, the bolt-action rifle, the fast normal prime lens. It exposes your shortcomings long before any of its own flaws come into play. The perfect tool for a student to use isn’t the one that does anything you want—it’s the one that makes you choose what to want.

Everybody likes presents, right?

A friend gives you a good book that she thinks you’ll like. How should you respond?

A) Wow, you don’t know me at all.
B) I like your shoes!
C) Thank you!

Lots of us would just say “Thank you!”, without blushing or refusing to accept, but we often have trouble knowing how to respond to compliments. We get embarrassed; we deny everything; we change the subject. Why not just gracefully accept the compliment? Accepting compliments strengthens your strengths and deepens your relationships.

Next time someone offers you praise or appreciation, try this:

1. Listen attentively without interrupting. Make eye contact if you can.
2. Let the compliment sink in for a moment. Let it be true.
3. Say “Thank you.”

That’s all it takes!

If you want to, you can say why you appreciate it:

  • how it makes you feel to hear it (“I’m really pleased to hear that.”)
  • which of your personal values is being acknowledged (“Social justice is important to me.”)
  • if you don’t agree with the compliment, you can still appreciate the giver’s intent (“You’re so kind to say so!”)