Advice and Insights for Modern Daters

The Pointless Pen Pal

You’ve been chatting for weeks and still haven’t met in real life — how do you know when it’s time to move on from a digital penpal? Molly offers a solution. 

Q. I “met” this guy on a dating app and talked to him for a few weeks before meeting each other came up. I wasn’t sure I was ready, and he later admitted he wasn’t sure either, since he was still trying to get over his last relationship. Since then, we’ve kept talking, but the conversation has really fizzled out. Now I feel like I’m the only one keeping it alive. I’m so confused, and I do like him, but I’m not sure it’s worth hanging onto. Help!
Lauren, 25, Denver, CO

A. Your letter brings up a big problem with online dating: how easy it is to get caught in the back and forth, when really, isn’t the goal of using a dating app to get off the app?

Here is my take on your specific situation: at some point, there was a desire on each of your ends to meet. For a multitude of reasons, each of you got cold feet at different points. In the end, you didn’t meet at all. Now the conversation feels forced, when at one point, it seemed fun.

The moral of this story? It’s important to meet IRL (sorry for the shameless plug!) ASAP. We take surveys of our members all the time, and have found that the majority of people (67 percent) who end up going on a date only talk for two or three days before exchanging numbers and, presumably, making plans to meet. The point of a dating app is to facilitate a meeting — not to create an online-only relationship. You should not have wasted time messaging with this guy if you were too nervous to meet in person, and he should not have been on the app if he still had hang-ups about his previous relationship.

That being said, I understand that meeting someone off a dating app can be nerve-wracking, even for experienced daters. Your anxiety was most likely elevated by the fact that you spent so much time messaging and had built up an idea of this person in your head, when the reality is, you don’t actually know him at all.

I suggest throwing this one back in the online dating sea for a few reasons: one, you feel like you’re doing all the work, which is never fun. He also admitted to you that he’s still trying to get over his break-up. You know what your reaction needs to be to that? Nexttt. It is not your job to play therapist to this guy, or to help him get over his previous relationship.

In the future, try to view dating app conversations as a means to get to the “main event” — an actual date. There is no way to assess whether or not you two will have in-person chemistry without actually taking the conversation offline.

Also: make sure you meet in a well-populated place, and make sure your friends know where you’re going and who you’re meeting. These are important online dating safety tips for anyone, but they will also help you feel less nervous. If you’re relaxed and have a plan you’re comfortable with, you’ll be more likely to hit it off.

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