November 6, 2018

Part 5 – How to Actually Meet Someone Online and Not Swipe Into the Void

How to Actually Send a Message Someone Will Want to Respond To

(If you’re just joining us, check out Parts 1-4!)

Tip #5 What To Say

Most people get stumped at the messaging part and totally whiff it. They either don’t say anything at all, or they default to something underwhelming like “Hi.”

Hi” is a bad message because it puts the burden on the recipient to keep the conversation going. For example:

Person 1: Hi

Person 2: Hi


In the improv comedy world, the first rule is that in a scene, you always say YES, AND. Example:

Person 1: Wow, that’s a really cool parrot on your shoulder.
Person 2: Thanks! And that’s a really cool – OMG is that a porcupine on your shoulder?

I’m not saying the above example is funny, but at least it has momentum. Person 2 accepts the premise (parrot on the shoulder) and adds to it. It keeps the scene going. Otherwise, it looks like this:

Person 1: Wow, that’s a really cool parrot on your shoulder.

Person 2: Thanks.


Not only is that definitely not funny, but it goes nowhere, which is one of the biggest problems online. Now Person 1 has to think of something else to say and in both the improv and online worlds, that’s a huge no-no.

If you want to send a message someone will actually respond to, take a look at the below and see how the “yes, and” principle applies. The “and” is the question, which makes it easy for the other person to respond to you.

Person 1: Hi! Where are you in that second photo? Is that Istanbul?

Person 2: Hi! Yes, it is! I just went there for the first time in May. Have you been?

Person 1: How’d you like it? My mom is Turkish and most of her family lives in Istanbul, so I’ve been going there to visit most of my life. What brought you there?

Person 2: That’s so cool. I loved it. One of the most beautiful places I’ve been. I went because I try to visit a new city each year and I heard good things. Where else do you like to travel?

The above flows because it has momentum. Each message ends in a question. They don’t have to talk about Istanbul forever, but it’s a great starting point.

Your initial messages do not have to be:

  • hilariously funny

  • super creative

  • witty

  • flirtatious

The only thing you need to be is: conversational and interested. All the other stuff comes later if and when you meet each other.

Finding something specific in the person’s profile to comment on makes it a lot more likely they’ll respond.

(Bear this in mind when it comes to your profile. Make sure it’s not so generic it would difficult to pick something out to start a conversation.)

Yes. And? Yes. And? Yes. And? Let that be your new online mantra!

See you tomorrow for Part 6!