November 7, 2018

Part 6 – How to Actually Meet Someone Online and Not Swipe Into the Void

How to Actually Go From Chatting to Meeting In Person

If your online chatting goes nowhere more often that not, you’re not alone. There are millions and millions of people who have the same experience.

Partly, this is necessary. Those initial messages are a way for you to determine if this person is a potential date. Most of the time, people will do something or say something to take themselves out of the running, so-to-speak.

The “weeding out” is par for the course and it’s a good thing.

What isn’t good is when the only reason two interested people don’t go out because they get distracted, lose the conversational momentum, or drift into chat buddy status.

What a huge waste of time if you’re looking for an actual IRL relationship!

Tip #6 Pivot!

You might hesitate to be the one to broach the IRL date subject for fear of being too forward, desperate or because you feel it’s the other person’s “job” to ask you out.

Do you want to meet someone or don’t you?? If you want to have a chatting buddy and spend more of your life swiping into the void, hang on to those old beliefs.


Once you’ve been having a back and forth about Istanbul, your holiday travel plans, your favorite ramen spot, etc, it’s time to pivot the conversation to planning an actual date.

There is no exact formula for when to pivot. Some people suggest a pivot after 4 messages. 4 might or might not be enough in any given situation.

My advice? Rather than focus on one number, you should pivot when you feel like you’ve established some rapport.

For Example:

You’re so right, Fatburger is so much better than In-N-Out! How come everyone doesn’t agree with us?? I think that warrants us at least having a drink or cup of coffee. Let me know if you’re up for it!


Well, you have great taste in Halloween costumes! Let me know if you’d like to get together for a drink sometime soon.


It’s kind of a long story of how I ended up living in Alaska for a year. I’ll tell you in person if you’re interested! 🙂 Wanna grab a tea or a smoothie sometime?

The above aren’t “clever” or “playing it cool” – they’re straightforwardly letting the other person know you’re not here for a chatting buddy, you’re here for a date. It puts the ball in their court

LADIES, I’M TALKING TO YOU! This isn’t “pursuing” a guy – it’s giving him a chance to take the ball and run with it.

Otherwise, it’s far too easy for the momentum of that conversation to be lost – and then… womp womp. You end up feel like online dating is a waste of your time. You will lose some folks at this stage – but that’s OK.


Some people have no intention of meeting up. Some people aren’t the person they’re representing themselves to be. Some people are looking to hookup, and if you’re trying to have an actual conversation, they’re not interested.

Remember your end game.

The messaging part will and should weed some people out of consideration. That’s fine! NO more time wasted and now you’re free to move on to someone who is actually on the same page as you.