My conversations on dating apps always stop. What might I be doing wrong?


rusrinus asks:

I am a straight male and have been on multiple dating sites for a very long time with no success and have only met one person in all these years. Every time I contact someone who seems especially promising she always stops responding without things ever getting very far. In the past she usually didn’t respond to the initial message at all but more recently they have been replying more.

For the ones that do reply initially, the follow-up replies always stop within 2-3 emails and we never meet. Any advice on what I might be doing wrong?

Demetrius says:

Considering you spelled everything correctly in your question, and your correct usage of grammar and syntax, I doubt it’s a quality of the messages issue. With that said, the possibilities are endless, though I can think of a few reasons why you’re getting a few short messages and then things abruptly change.

My first idea whenever I’m posed with this question is to ask you what the content of your messages is. If your 3 messages are cookie cutter “good” messages that are just small talk, I could see why you’re not gaining any traction. The two worst types of messages you can send on a dating app are vulgar messages (unless specifically told to do so) and messages that sound like the sort of conversation you’d have with a coworker you’d never want to see outside of work. If your conversations look like this….


…then why would anyone want to continue this conversation? A lot of times you get stuck in a loop with a stranger where all you discuss is the past and the future (How was your weekend? Any plans for the weekend?) instead of trying to plan something for the future. It’s possible you’re getting stuck in the trap of niceties and if that’s the case, I could see why your messages aren’t going anywhere. To avoid this, ask questions that cannot be answered in one word. Asking how something is, or went, or was can be answered with “Good”, but asking someone about a specific interest is pretty hard to answer monosyllabically. Ask pointed questions that serve one of these purposes. Either ask questions that help you determine if you want to go on a date with this person (i.e. check off your list of deal breakers), or date planning. If you’re doing neither one of those things, you’re failing at messaging in a meaningful way.

Another reason your messages might be producing a failure-to-launch is that you’re just putting too much content into your messages. What you want to develop with your messages is either a banter, or a planning session, not an interview. If you’re going for banter, you might feel tempted to load all your messages with multiple questions to get as much information in a short amount of time, but you need to resist that urge. If you give someone 10 questions to answer over 3 paragraphs, messaging you becomes a chore and the opposite of flirty banter. Dry discourse maybe? I dunno what to call it, but you get what I’m saying. Ask one question per message, and don’t double up on messages unless you’re responding to something they asked.

Finally, and this is by no means the only other issue, but one of the main issues, is that you’re just having a run of bad luck. Your messages could be perfectly fine, you could just be meeting people who quickly lose interest for a variety of reasons that have nothing to do with your messages. It happens, it’s a natural part of dating that you can’t avoid regardless of your preparation.  They could lose interest after matching and messaging for a number of reasons, like figuring out you aren’t a good match, or they’ve already met someone else, or they’re not all that interested in online dating except to use it as an ego boost. It happens, and you just have the misfortune of meeting these sort of people back to back. There’s not much you can do to avoid this, so just chalk it up to bad luck and press onward.

If you take my advice, to make sure you’re messaging with two goals in mind, then you’re sure to improve your chances of meeting people who you match and message with. Remember to avoid the “Hey, how’s it going” cycle and you’ll do fine.

Good Luck Out There.

One thought on “My conversations on dating apps always stop. What might I be doing wrong?

  1. Pingback: No reply after asking her out. What went wrong? | Tao of Indifference

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