Tag Archives: meeting in person

Ask Emily: How Long Should I Wait Before Making a Date?

Lunch Date
Hi Emily, I learn so much from your podcasts! I am 36 and recently separated from a 16-year relationship. After waiting eight months, I decided I was ready to start dating again. A few colleagues of mine recommended some dating apps, so I checked them out. I went on two OKCupid dates and they went horribly. Then I gave it one last shot and started talking to a guy six years older than me. We have been talking for two weeks but haven't met in person yet. So far, our connection has been great! So here’s my question for you: is there a certain timeline to meet this guy and move forward from there? What do you suggest when it comes to going from cyber- and phone-chatting to meeting IRL? Read more