Advice and Insights for Modern Daters

Conversation Stopper

Molly counsels a letter writer whose dating app conversations fail to lead to dates.  

Q. I seriously suck at dating app conversations and I feel like it’s affecting my ability to get actual dates set up. Every single conversation seems to go the same — “Hi, how’s your week going,” “Good, yours?” — and then more boring talk about our jobs before it just drops off completely. I feel like I must be boring every single guy, and like success on apps relies so heavily on how funny or witty you can be to catch someone’s attention. I think I’m fun and cool in person. It’s just on these apps that I feel totally inadequate because of my lack of interesting texting-with-strangers skills.

-Kayla C., 26, Washington DC

A. All right, Kayla — first of all, know this: if you’re matching with people, you’ve already won half the battle. Obviously, dating apps rely heavily on visual appeal. The fact  you’re matching with men and engaging in back-and-forth conversation is huge.

But that doesn’t solve your problem — which is that your conversations stall, your matches drop off, and you’re left wondering what’s “wrong” with your personality.

Let’s get one thing straight — nothing is “wrong” with your personality. Engaging in conversation on dating apps is a skill that takes practice. Very few men or women feel “super funny and witty” while engaging with complete strangers. Think of it this way: many people have anxiety talking to their barista, and all that person does is make their coffee. Of course most people will experience pressure to entertain when talking to someone they might end up…marrying. 

The majority of Hinge conversations that lead to a date consist of 15-20 messages and occur over a two to four day period.*

Here is the truth about dating apps: the entire premise (texting a stranger) is awkward and unnatural. Most people respond to this awkwardness by providing safe, boring responses — responses that lead to stalled conversations and drop-offs. 

People do this because they don’t want to turn the other person off, which is understandable. But when you’re texting, you have nothing but words to go off of — there is no body language to read, no tone of voice — so if you aren’t at least a little bit “zany,” you run the risk of your match losing interest. Most Hinge users, for example, send between 15-20 messages over two to four days before mutually agreeing to go on a date.* We need to get you to 15 messages, and the best way to do that is to be fun, be honest, and provide detail. 

Here’s an example: let’s say you match with “Brian,” and he asks what you’re up to that evening. Most people in this situation would give a safe response, or one that makes them look “cool.” This might materialize in the following Zzzzz-worthy replies:

  • “Hanging at my friend’s place. You?” 
  • “Just left the gym. What about you?
  • “Still at work unfortunately. How about you?”

Now, there’s nothing wrong with these replies, but they really don’t tell Brian anything “real” about you or get you any closer to deciding if you two might be compatible. Taking the “honest and detailed” approach, your replies would look more like this:

  • “At my friend’s apartment trying to decide what to order on Seamless. We’re starving! Want to bring us some fries? :)”
  • “Just left the gym — took the hardest class ever! I looked like a complete spaz, but whatever, it’s the effort that counts, right?”
  • “Burning the midnight oil at the office, ugh. I just started a new job and trying to make a good impression. Fingers crossed!”

Now Brian has something to work with as he crafts his response.  He knows a lot more about your personality, and he’s got some insight into how you spend your time. Brian now views you as a real person with a real life and real job and real friends. He’s picturing you in your pal’s apartment pouring over Seamless menus; he’s got you struggling through a workout in his head; he knows you’re a hard worker who is still humble enough to worry about making a good impression. These replies were detailed, thoughtful, and will (hopefully) elicit a similarly candid response or set of follow-up questions.

Kayla, I guarantee if you give more to your matches in terms of conversation, you will get more in return. Do not be afraid to speak your mind or tell your matches exactly what you’re doing when they ask — even if it seems lame or weird to you. Honesty is uncommon and refreshing.

Remember, on the other side of that screen is an actual human being, not a robot. Realness is what wins with people — not safe or “cool.” Show people who you are and watch the dates roll in.

*Hinge user data

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Molly Fedick is the Editor-in-Chief of IRL. She has written extensively on the role of technology in modern dating for publications including Glamour, NBC, the Chicago Tribune, Elite Daily, and Huffington Post. You can follow her on Twitter and Instagram @mylifeasmolly. Send her questions at


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