Tag Archives: choose dates

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

How to choose between two guys

I’m in the middle of catching up on The Bachelorette. No spoilers, please! I’m pretty behind. Even though I’m early in the season, I’ve formed some fan feelings for a few of the guys. It looks like Andi has some very serious feelings for a bunch of them as well. It got me thinking about deciding between men. This isn’t just a problem in reality TV competition shows. It happens in real life. With online dating and busy schedules, a lot of my friends wind up stacking dates and getting into separate relationships at the same time. I know you women out there who can’t even find one dateable guy think this is insane. But, trust me, when it rains, it pours. You could be dealing with a very similar situation in the near future. Here’s how I advise my friends when they’re dealing with choosing between two guys. Read more