How To Date
I’m happily engaged. I think we might get married next month? But I sat down with a friend recently who is dating – and in San Francisco, no less.
Our meeting was ostensibly a business lunch but quickly turned into a “But how are you doing personally?” conversation. The answer: her dating life was difficult.
My friend is an ambitious professional. She’s attractive, smart, and knows what she wants. Yet, over lunch, she shared a multitude of stories about getting ghosted, men pursuing one-night stands, and general frustration.
I didn’t have any answers, of course. I can’t solve her situation. It has been over a year since going on what I hope to be my last first date – and 20 years since I started dating. I’ve been on over 1,000 first dates, so I do have some experience.
In the spirit of my new book This Might Work: A Collection of How-Tos, I thought I’d write a comprehensive article on how to date.
The Biggest Turn-Off
The most under-addressed aspect of dating is neediness. When you're going on a first date, or even a fifth, neediness is the kiss of death. To illustrate it, I’ll share the story of the first time I was fired from a job.
One of my first jobs out of college was as a personal trainer in San Francisco. Gyms are a sales-heavy environment. In order to be in the business, you have to sell clients.
My job entailed teaching a step aerobics class at 5:00 a.m. and then spending the rest of the day walking the gym floor trying to persuade members to hire me. I lasted a week.
On Thursday, my manager sat me down and said if I did not close any new clients by Friday, I'd be fired. I tried my best. And I'm sure I came across as extremely needy. Who doesn't love a personal trainer with the vibe, “Hire me, or I’ll get fired tomorrow!”
There's no better way to not go on dates than to really need to go on dates. It is simple: don’t approach people or try to date if you feel needy. Fix your attitude first.
13 Dates in 3 Days
In my mid-20s, I was living in a house with several roommates in San Francisco. My roommate, who was at the time engaged, had seen me through several short-term relationships. He had observed the same pattern: I would meet somebody, go on a date, fall into bed with them, and then spend the next three months in a relationship.
He challenged me to go on three first dates with three different people, before going on the second date with any of them. He wanted me to increase my volume.
To make things interesting, we set some stakes. If he won – if I was not able to go on three first dates with three different people – then I would make him and his fiancée a homemade multi-course meal. If I won, he would make me and my date an elaborate meal. It helped that he was a gourmet chef.
I went on a few first dates over the following month, but none that merited a second. Then, one Thursday night, another roommate introduced me to someone, and we immediately hit it off. We made plans to go on a date on a Sunday. But she was visiting my roommate on Friday, and we ended up spending time together. (As I recall, we spent the evening clambering around a public jungle gym?) There was a kiss at the end of that evening, so it was definitely a first date.
And we still had plans to go to lunch on Sunday! This meant I needed to go on at least two more dates on Saturday or Sunday morning before our scheduled lunch to win the bet!
I did everything conceivable to win. At the time, the only dating apps available were OkCupid and Match.com. The following day, I messaged perhaps a hundred people. I called a dozen friends and asked them who they knew. I met somebody in a burrito shop and asked if she’d like to go for a walk.
I ended up going on 13 dates from Saturday morning until Sunday noon. (Or 14 if you count going on a date with a couple – I didn’t realize that they would both be there until I showed up for coffee.)
In the end, I won the bet. And I learned that when I was sufficiently motivated, I could generate a lot of dates in a very short period of time.
Where To Date
Bars - One of the few things that I have never done is pick up women in bars. I know it's an environment where people meet, but even before I stopped drinking alcohol, it was never the kind of environment that I particularly enjoyed. My view? Bars are overrated.
Coffee Shops – Long before I owned a coffee shop, I was prone to starting up conversations with people in cafes. Coffee shops offer a great third space – not work, not home – to meet people.
Speed Dating – I've been to a couple of speed dating events. Like all events, it really matters how well it's organized. Most speed dating events aren't very well run, but if you can find one that is, with an appropriate gender balance, it can work.
Niche Hobbies – I'll talk later about being your weird self while dating. For now, though, I think one of the most useful ways to meet somebody is doing things that you love to do and that are very niche. My dear friend Marie met her husband at Gamba Camp!
Organized Co-ed Sports – Organized co-ed sports are a great way to meet people: kickball leagues, running clubs, etc. You're not there to date; you're there to play a game or exercise. But the quality of people is likely higher and they often go out for drinks afterwards.
Non-organized Sports – Another great place to meet people is in environments where everyone is practicing a shared skill outside of an organized setting. Indoor climbing gyms are excellent. Pickup basketball games, etc. These require more willingness to introduce yourself to strangers, but the payoff is worth it.
Social Dancing – The most effective environment I have found for going on dates is social dancing – Argentine tango, Salsa, West Coast Swing, etc. Social dancing provides a functional environment where you can meet and be close to a lot of people in a short period of time. You see them in a vulnerable place, trying to learn something new, being awkward and funny together, and getting a more unfiltered view into who that person is.b
Ask Everyone for Help
One of the most ridiculous things that I did in my years-long effort to find a partner was ask everybody I knew to make introductions.
Over the course of three or four months, I reached out to a few dozen professional colleagues – people I only knew as speakers on stage at Responsive Conference or clients of Zander Media – and asked them to make personal introductions.
My only qualifications were that they were people I admired, and I was intimidated to ask them for help.
I told them:
- I'm a 30-something guy.
- I'm a successful bootstrapped entrepreneur.
- I'm looking for a life partner.
- I'm willing to travel anywhere in the world for a first date.
- Would you be willing to make three to five introductions to eligible women that you think I would connect with?
It was incredibly intimidating. But everybody that I talked to was supportive and agreed to help.
Increasing Your Luck Surface Area
One of my favorite phrases is “Increase your luck surface area.” The underlying message is that you get lucky through hard work. Of course, luck matters a great deal. I was born a white man in America, after all! But in dating and in life, creating the conditions where you are likely to get lucky makes a great deal of difference.
In the case of dating, that means that you're more likely to meet people when you are going out several nights a week than if you're staying at home. You're more likely to meet clients when you go to business conferences. You're more likely to land a new job if you ask current and former professional colleagues for introductions.
All of these things take hard work. Put yourself in the condition where you are more likely to be successful – and you will be.
Dating Apps Are Slot Machines
I met my fiancée on Bumble. Almost certainly, I’d never have met her otherwise. But dating apps aren’t designed to get you a date. They’re designed to keep you on the screen.
Dating apps are incentivized to keep you on the app—that’s their business model.
Treat the apps with discipline – spend an allotted amount of time on the apps each day – just like you would going to the gym or brushing your teeth. Treat using dating apps as a tool, not a distraction.
Set aside specific times to match and to message – Don't let yourself doom scroll on dating apps. Instead, set aside a few minutes or even an hour each day to match with people and message with them.
Get off the apps – The thing that dating apps can do is connect you with people you might not otherwise have met. Now that you’ve met them, get off the app! As soon as possible, take that digital conversation to text, a phone call, or in real life.
Communicate like a human – There are a lot of scammers and people wasting time. If you get a bad vibe off somebody, move on quickly.
Most People Are Flaky
Being reliable – simply doing what you say you're going to do – is a big advantage. Because, unfortunately, most people are flaky.
This is triply true in dating where inherent flakiness is combined with all sorts of hang-ups, unprocessed trauma, and a lack of clarity as to what someone actually wants.
It's just a sad fact that you're going to have to wade through a lot of unreliable people to find some diamonds in the rough.
You Get Ahead By Being Yourself
The single biggest thing that you can do to increase your odds of a good match is to be true to who you actually are.
I like phone calls. And so, what my fiancée and I have come to call “date 0” was a two-hour phone call. We covered a lot of ground in that first conversation that might not otherwise have been things that people talk about on a first date. On our actual first date – which happened the next day – we shared intimate details about our families and past relationships.
Of course you want to present a polished version of yourself. I washed my car before meeting my fiancée for the first time in case she wanted me to drop her off at her front door at the end of the night. But you also have to be yourself, so that you don't get found out later for having lied about who you really are.
The Goal Should Be Connection
Most of us early in our dating lives are trying to get something – to get laid, to find love, whatever it is. And when we approach dating from that place of need, it rarely works.
If all you're trying to do is assess whether this person is a good long-term romantic match, you're in for a long road.
Your goal should be to connect with the person you're talking to, first. And then let everything else happen from there.
Dating is Selling
Everything that I’ve ever talked about selling applies to dating too.
Know Yourself
If you don't know what you're looking for, you're much less likely to find it. Unfortunately, in order to know what you're looking for, you have to know yourself. Self-knowledge in dating – or choosing any kind of partner – is the ultimate competitive advantage.
Tell Compelling Stories
I talked extensively about storytelling and how to tell your own story so simply and effectively. Telling stories about yourself that are real, compelling, authentic, and vulnerable will go a long way to connecting on a first date.
Play More
My fiancée finds me hilarious and I'm never quite sure why. But I have learned that when I am most authentically myself – the silliest, most playful version of myself – I can be quite compelling. Don’t try to force humor, but when you’re playful you’re more likely to connect with others.
Ask Sincere Questions
I asked my fiancée all sorts of vulnerable questions on our first phone call and first in-person date. I caveated them with “please don’t feel obliged to answer, and I was wondering…”. But I did ask. Ask the questions that you're sincerely curious about, and they get to the heart of who the other person is.
Be Flexible with the Outcome
One of the 13 dates I went on was with somebody who stated very quickly that she wasn’t in a good place to date. But she offered that if I’d like to, we could still get together over coffee.
We ended up climbing trees in San Francisco’s Golden Gate Park, sitting in the tops of trees and sharing book recommendations.
I don’t remember her name, but I do recall the unexpected delight that this “non-date” turned into a sincere friendship.
When you’re flexible with the outcome, you can often get more than you expected.
Prioritizing Yourself
Don't burn yourself out trying to date. It's tempting to hope that just the next minute, the next match, or the next first date will land you the relationship that you want. It probably won't.
If you don't prioritize yourself over your dating prospects, you likely won't get very many dates, and you certainly won't match with somebody who's actually a good fit.
3 Things I’ve Loved This Week
Quote I’m Considering:
"My view is that there are only a handful of things that are really important, and you devote all your time to those and forget everything else. If you try to do all thousand things, answer all thousand phone calls, you will dilute your efforts in those areas that are really essential." -Larry Ellison
Article I’m Reading:
We’re all thinking a lot about AI, and how it is changing how we work. My friend David forwarded me this article, and I’ve been thinking a lot about it.
The basic premise is that in a world where intelligence is abundant, what are the most valuable or scarce resources?
One item that the author doesn’t say is “Human Connection,” which I’m willing to bet on, and I don’t agree with everything he says about “Trust and Accountability.” In general, though, I think the questions he poses are worth considering.
Book I’ve Loved:
My friend and Responsive Conference 2026 speaker Rebecca Hinds just published a new book Your Best Meeting Ever.
We sat down for a podcast interview about the book, which will be coming out next week. (If you aren’t subscribed to the podcast on Spotify – what are you waiting for?!)
Seth Godin said of Rebecca’s book, “Meetings are broken. This book fixes them – if we care enough to take action.”
More even than the tactics she shares, the book is beautiful and lovingly written.
Want more?
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The Snafu Conference is an immersive 1-day experience about authentic selling in a chaotic world. The summit will take place on March 5, 2026 at the Oakland Museum of California. Ticket prices go up soon, so get yours now!
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Responsive Conference is coming back in 2026! With AI and a changing economy, our jobs and careers are changing faster than most of us can adapt. Attend Responsive Conference and learn how to keep up with change. Ticket prices go up soon, so don't wait!
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Until next week,
Robin
