Updated October 2018
I wrote this article about how to do well on first dates (because I was going on a lot of first dates and I was struck by how awkward they can be). I realized that the tool works just as well when you grab a cup of coffee or lunch with a new networking partner…which is basically another form of first date. So whether you are looking for a referral partner or a spouse, I hope this will help!
Most of us dread first dates. It’s a weird combination of job interview, etiquette test, and fashion show that we submit to in the hopes that a) we like the other person and b) the other person likes us. And the most “useful” advice we get from family and friends is to be ourselves and have fun. Sure, as if it’s that easy when you’re in the spotlight…
How to Make Conversations Easier
But I can give you a tool that can make your first dates easier. (I didn’t say easy – I said easier.) A lot of the stress on first dates comes from feeling that we need to be fantastic – you know, funny, charming, interesting, and smart all at the same time. That’s a lot of pressure and it would make anyone freak out. The way to avoid this is to put the focus on your date – but in a way that doesn’t make the other person freak out either. How do you do this?
Ask really good questions … and let them talk.
The emphasis here is on good questions. When we’re with people we don’t know well, we often fall into a trap of asking questions that have simple, closed answers. We then give our answer and we’re back to staring at each other over our appetizer. For example:
“Where did you grow up?”
“Here in Chicago. How about you?”
(Insert awkward pause as both parties try to think of another topic and mentally curse their friend that set them up.)
The Next Question™
There is actually a trick to asking good questions, I call it The Next Question™. Instead of asking questions that have simple, closed-off responses, ask questions that require open, essay-type answers. Then, use the answer that your date gave you to ask another question. For example, if they grew up in New York, you could ask: How did you like New York? What was the best part about growing up there? What brought you to Chicago? And then based on their answer, you’ll have a while new slate of questions to ask.
It’s something you do naturally with people you know well – you dig in to the topics that are important to them. We’re just taking that same process and deliberately applying it to a conversation with someone new.
A big caveat – don’t become an interrogator and shoot off questions rapid-fire. That will have a totally different effect on your date. You can still share stuff about yourself, and there will still and a back and forth. The goal is to find a flow to the conversation. In fact, you’ll find that your date is more likely to ask you really good questions and to be engaged in the interaction because of the interest you are showing.
This works because, ironically, the best way to be fascinating to others is to be fascinated in them. When someone asks about us and listens to what we say, it makes a huge impression. As people, we like others who are interested in us and our perspective and we’re more likely to be interested in them in return. So you can take the pressure off of yourself to be amazing without feeling that you aren’t a good date. And then you really can be yourself and have fun.
And that’s the recipe for a great first date.