A lot of people don’t like dating. You hear a lot of gripes about how people were weird on a first date, how the first date had logistical snafus, that the lack of follow-through was a let-down. I have friends that planned very thoughtful experiences – some show that has a musician you think they’d love, some exhibit at a museum you think you’d both find so interesting. And so many times it’s a drag. 

I think a lot of the complaints about dating come from some combination of high expectations and overextending oneself. And many people overextend themselves in dating – spending too much time and effort messaging people and too much time and effort and money in planning dates. 

I’m not on the market, but I think the approach I used for dating would be useful to a lot of people who want what I call casual intimacy – meaningful connections with people without extensive commitment. Dating this way creates options – you can stay the course or grow into a relationship. 

Maybe we can call it dating entrepreneurially (there’s got to be a better name for it – please send it my way). A central paradigm for entrepreneurship is experimentation, by placing bets that have limited downside and unlimited upside. This is where a lot of people go wrong with dating – they overextend their resources. So here’s my roadmap:

  • Online dating is essential. It makes it way easier to put yourself out there, it’s flexible, and we’re all more sophisticated with our online personas (and deciphering them) than ever. Will you ever be surprised? Of course. Isn’t that some of the fun of it?
  • You have to optimize the amount of time you spend messaging people, while making it appear you are being purposeful but not in a rush. 
    • Establish rapport quickly. Make sure you’re getting someone to actually commit to a response, something where they’re putting themselves out there.
    • Then after about seven exchanges (you said something and the other person said something), segue into asking for a date. Seven means the other person is interested and you are not acting before people get bored. Dating is a momentum game. And it requires mutual commitment. That’s why you ask for the date. 
  • They want to get a date: great! Now ask for the number. The number reflects commitment, trust, and heightens the sense of excitement – where will this go next?
  • So what kind of date should you ask for. Although I myself am not drinking, I recommend getting a drink (you can even try caveating that you yourself won’t be drinking but drinks would be fun anyways). Why drinks?
    • Drinks don’t take much time to get – you can have a drink in half an hour
    • A good bar is pleasantly busy but not distractingly so
    • If you don’t see chemistry after one drink, you can leave
    • It’s easy to schedule drinks early enough in the evening that it fills the gap between work hours and evening hours (again, you can leave to enjoy your evening if you’re done)
    • Drinks are relatively inexpensive, relative to dinner. And the costs are predictable. If you’re like me, you even calculate the expected value of the drinks for…your preferred outcome for the date. And then use that as a benchmark for making decisions about how much to put into a date as it unfolds. 
    • You can pick a favorite bar that’s close to you that others don’t know as well, so that will give some novelty. This saves you time and effort
    • The bartenders will get to know you and give you good service, and you’ll enjoy their company even if you don’t enjoy your date
    • Sitting next to someone at the bar is just the right amount of intimacy, without the sterility of sitting across from each other at a table
    • This also means you two are not being distracted by some other event or subject (e.g. looking at paintings at a museum). I would usually try to sit at the end of a bar where it was relatively less busy, and sit so my date faced me away from the crowd
  • So what do you talk about on your date? That will have to wait for another post. I developed a pattern of conversation that made it very easy to sustain a conversation, and make it so we both felt like we could be open and share things about ourselves. 

Honestly, I got so good at this approach that I would often look up to see who I had a date with on the walk to the date. It works! But while I’ve outlined the procedural aspect of effective dating, the substantive aspect was essential for me. Dating was a practice, a way to learn about people and their worlds, and to share your own. Causal intimacy can’t happen without intimacy. So enjoy yourself, let yourself explore, but make it easy to explore. Have fun!