Escape the Messaging Black Hole on Dating Apps

Have you ever started chatting with someone you matched with on a dating app, only to get trapped in a neverending conversation that never leads to a date?

It’s ironic that dating apps, which are made for cutting-to-the-chase and going out on dates, have become just as confusing as the non-virtual dating scene.

Last year, me and a bunch of girlfriends decided to take on the dating app world. We all lived in different cities across the country, so we created a group chat to keep each other posted on our progress.

We quickly noticed a pattern in all of our dating app experiences. It went like this: we would match with someone, start chatting, and never stop chatting. Each of would ask, “If I already matched with this guy and we’re clearly interested in talking, isn’t it obvious that I want to be asked out? Isn’t that literally the reason why we’re on a dating app?”

So, I sought out some male advice. I met up with my friend Johnny, who was a regular on dating apps, and I asked why guys weren’t asking us out but just wanted to chat. What he told me was very eye-opening. He said, “Chatting with a girl on a dating app is a lot like talking to a girl at a bar. Just because she’s engaging in conversation at the bar, it’s not necessarily a green light to ask her out. She could still say no.”

He explained that no matter how many positive signals a guy is getting from a girl, he’ll still be nervous and unsure until she explicitly says “yes” to going out. So he recommended a couple ways to encourage conversation on a dating app that ends with a date.

Beware of affirmation seekers

Some guys (and women) use dating apps to get an ego boost, to be reassured in their attractiveness and desirability. They’re not looking to actually pursue a relationship, but simply want to flirt and feel like someone wants them.

Texting is innocent enough and doesn’t require any real commitment, so they feel safe stringing someone along. Once a woman has made it clear she’s interested, he will quickly lose interest and won’t want to take communication offline. To weed out the affirmation seekers, try the next two conversation tips.

Tip #1: Talk about specific places you like

If you’re messaging with someone who lives nearby, use to it your advantage. Ask him something simple like, “How long have you been living in x place” and then follow it up with, “What are your favorite things to do?” He’ll probably start mentioning hobbies or places he likes to go to.

Once he does, say something along the lines of, “That’s sounds like fun, I’ve always wanted to do that/go there!” If he doesn’t offer specific places he likes to go to, ask him more pointedly about restaurants he recommends and say, “I’ll definitely have to check that out!”

This will open the door for him to say, “I’d love to take you there,” or “Let’s meet up there sometime!”

Steering the conversation to a topic where asking you out is more natural will help him to feel comfortable and confident. Asking you out right after you finish explaining your college major or how many sibling you have might feel random to him, so mentioning specific places you want to go to makes his question much easier.

Tip #2: Say you’d rather talk in person

If you find yourself in the chat black hole and he’s not picking up on your hints, be upfront. If he’s genuinely interested in getting to know you better, he won’t have a problem with you saying, “I’d love to explain this more in person sometime.” Actually, he’ll welcome it.

Unfortunately, guys (and girls) use the messaging feature in dating apps to burn through conversation topics that are meant for actual dates. If you feel like you’re revealing every interesting thing about yourself in the app, it’s definitely time to cut it off and say you’d prefer continuing the conversation in real life.

Using up all the first date conversation topics via texting is not respectful of your time and it shows a lack of intentionality and integrity on their part. If someone thinks they have a right to your time and energy without properly asking you out, then you have every right to kindly yet firmly say you’d rather continue to conversation over coffee. If they back out and don’t want to meet up, you will have saved yourself a lot of time and effort that will be better used on someone else.