The One Question You Should Never Have to Ask While on a Date

Guys (and ladies), next time you are romantically/sexually interested in someone, use eight simple and powerful words.
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Dating. It can get freakin' crazy town up in here.

One thing has been coming up a lot lately in conversations with clients and friends is the idea of first dates.

And what I realized is that the one question that you never want to have to ask on a date: "So, is this a date?"

I've been on dates (and non-dates) where that was the question one (or both of) us was asking ourselves. And if that is happening, then it's time to shift our strategy.

A long while back, I rebelled against dates. I resisted the idea of blowing $100 on someone I barely knew. Then I resisted my pattern of getting too physical, too quickly. We'd both be stuck in the dopamine and oxytocin roller coaster and we'd have no idea whether we actually liked or loved each other. We did know that we wanted to screw each other, though. And that's a great thing.

So then I shoved the pendulum in the other direction. I wanted to get to know women as friends, first. I want to know if I actually love hanging out with you. Because no matter how much great sex we have, we still have to be in each other's company in non-naked situations. Can we go on a four-hour car ride with each other and not want to duct tape each other's mouths? Can I have a blast with you at Target? Can we just chill out at home together and enjoy not talking? As long as there was initial physical attraction and chemistry, let's put that on hold so we can get to know each as humans, first. So from then on, it was coffee. Or gelato. Real simple and casual. No pressure! No risk! And I still believe in that overall strategy. I want a best friend and a lover.

But it's time to bring sexy back.

Because I noticed there was no spark on those dates. The vibe would already start off as friend zone. And therein lies the problem. If I want to find love, sex, romance, I have to create a space for it to show up. If you want to order love and sex, you gotta put them on menu.

My point is not about what you actually do on the date. The content is mostly irrelevant. It could be an espresso in Central Park. Sweaty salsa dancing in a dark corner of the local Cuban joint.

Picking out your favorite baboon at the zoo.

It's more about the context of the date.

One fine day I got the phone number of a woman I met and felt a vibe with. Normally, I would have said, "We should meet up sometime and grab coffee." And in my mind, I would have been thinking, "Let's see how the meet-up goes. If it goes well, we'll declare it a date retroactively. If it doesn't go well, it's ok because it was never a date to begin with! No risk!"

But with that approach, she doesn't know what to do.

"Is he even interested in me?"
"What should I wear?"
"Does he find me attractive?"
"Is he going to be treating me or are we splitting the check?"

All of which add stress and confusion for her.

So with this particular woman, I just said: "I want to take you on a date. What does your week look like?"

NO ambiguity.
NO hesitation.
NO "so you wouldn't wanna, kinda, sorta go out sometime, would you?"
NO "hanging out," "grabbing coffee," "grabbing a bite."

And there are several benefits of being bold and direct.


She knows what you're wanting.
She knows what's she's going into.
She gets to respond to your honesty.
It's clear who is inviting who and who should pay (you).
She will actually feel your desire for her. Which feels a lot different than covertly desiring something from her.
She can relax.


If she's not interested, you get to know right away. No need to waste time/money/energy/tears on finding out later.
You feel good that you were unapologetic in owning and declaring what you want.
You know that if she does say yes, that she knows it's a date, too. It's on.
You know that both you and her won't be playing any games or be stressed out in the ambiguity.
You've created a space for romance, flirtation and courtship to happen. And she gets to choose whether she wants to enter that space.

I spoke with several female friends about what I did and they all said something like, "Whoa, that's bold. I love it. Wish more guys did that." And to be honest, it was a new way for me. And it felt fucking great. I was energized. I was open to whatever answer she was going to give me.

So guys (and ladies), next time you are romantically/sexually interested in someone, use eight simple and powerful words: "I want to take you on a date."

And no matter what they say back, you'll be clear. Either it will be on, or it's not, and you can move on.

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