How To Have A Conversation On A Dating App (Hint: It’s Not That Hard)

9 min readDec 13, 2017


I never realized how bad people are at conversation until I started using dating apps. I have always considered myself pretty decent at conversation — I am sure there are some people who find me awkward, or just aren’t a fan of mine for whatever reason. But, for the most part, I consider myself someone who can talk about a variety of subjects, with a variety of people. I never realized how much “like attracts like” in that I am often surrounded by people who are similarly skilled at conversing. Whether through choice of school programs and extracurricular activities in college (I was a public relations major and I was in a sorority, both of which required a certain level of communications skills), or fields of work post-graduation (I work in nonprofits which tend to not only attract a wide variety of employees, but also a very diverse clientele), I’ve mostly always been around people who are pretty decent at holding a conversation.

Enter dating apps.

Trying to talk to men on dating apps is so horrifically painful. I didn’t know it was possible for people to be so horrendous at conversation. And to be fair, my male friends say women are just as bad, if not worse, and I don’t doubt that for a second. But, I date men, so my experience is only with men; however, I think a lot of what I am saying can be applied to any gender. A few month ago I wrote a “how to ask a woman out from a dating app” guide for men, but lately I have realized that people need even more basic instructions than that. They need to know simple tips for having a normal conversation.

I don’t know if these men are just HORRIBLE at conversation or just aren’t that interested in me (probably some of both depending on the person), but either way, in case people genuinely don’t know, I thought I would write some tips on having a conversation. Something I don’t think grown-ass people should need a lesson in, but apparently they do. So away we go.

Before I get started, I want to say, that I am a very straightforward person, who has no time or interest in the “games” or “rules” of dating. I have no issue with messaging first, even on non-Bumble apps, and I don’t even mind leading the conversation to an extent. I feel like if you want something (or someone) go for it — life is short, and we spend too much time overthinking our interactions on apps. While we are worried about who should message who first, or making sure we don’t respond right away so as not to seem over-eager, someone who would have been good for us might be meeting someone else who actually talks to them like a normal person. Plus, a guy that is going to be put off by the fact that I’m willing to message first is not my kind of guy anyway. But even with me putting in a lot more effort than some women are willing to put in, the results I get are horrific.

With that being said, here are a few tips on how to have an actual conversation. (This is strictly focusing on what happens once you’ve sent an initial message and someone replies to it. I’m not going to even get into how many of my awesome opening lines go ignored.)

No overly familiar pet names

Don’t call someone cutie, sweetie, babe, honey, etc. when you have never met them. The few people who might be okay with this are vastly outnumbered by the number of people who don’t like it. Just don’t risk it.

Nothing sexual

This shouldn’t even need to be said. But there shouldn’t be any sexual messages exchanged before a first meeting. Even if someone states in their bio that they aren’t looking for anything serious, or that they are interested in kink, or anything of that nature, they still deserve some respect and to be treated like a human. There is no need to get sexual within the first few messages.

Don’t expect the other person to lead the conversation, especially if you don’t give much information to work with.

Exhibit A: In this instance, the guy I matched with had kind of a vague bio compared to what I am normally interested in, but at least he wrote SOMETHING, and his photos were alright so I gave him a shot …

…I HATE this “just ask” mentality. You should be able to write a sentence or two about yourself in a bio, but if you choose not to, you better be prepared to lead the conversation because you aren’t giving me anything to go off of. I’m not going to spam you with interview-style questions just because you can’t even give me a starting point.

Exhibit B: A very common thing I notice is that men love to complain that women send boring openers on bumble (which is fair, women frequently complain about the boring openers that men send on every other app). But, when I go out of my way to send stuff other than “hey” or “how are you,” I often get a curt response that doesn’t really make me want to continue the conversation.

If someone reaches out, and you are interested in talking to them, talk to them! Be happy you got a unique opener and try to send them something unique in response, or at least ask them something about their profile.

Don’t act like you are entitled to someone (or assume someone else feels entitled just because they’re attractive)

I stole this screenshot from a friend:

I get that confidence can be attractive. But coming right out the gate with shallow comments isn’t the move. And acting like someone doesn’t need to have personality just because they are attractive is basically saying “I don’t care about what you have to say.” I know some people feel like they DON’T need to have personality because they are attractive but 1. Why encourage that behavior and 2. If you haven’t seen an indication of someone feeling this way, why automatically assume they feel so entitled? This guy took a funny “opening line” and ruined it immediately.

Ask questions — actual questions, not filler questions or interview-style questions

This is the BIGGEST issue I encounter on dating apps. People will either:

- Go through a serious of meaningless questions — where are you from? What are you looking for on here? How long have you been on here? This is BORING. It makes everything feel like an interview and it does NOT make me want to go on a date with you.

- Ask really vague boring questions that everyone asks — how was your day? How was your weekend? I once had to take a break from dating apps for a few weeks because I was so tired of answering how my day was all the time. That was legitimately the main reason I needed a break. If you can’t come up with something better to ask, either you are boring, or the person you are talking to is boring and isn’t giving you anything else to work with. I get asking this once you’ve been messaging a few days if you ACTUALLY want to know how their day was. But this shouldn’t be your daily go-to conversation starter.


A conversation should be a back and forth. Not this:

I stopped responding after this. Because aside from “how is your night going” (which really falls into the boring question category but I let it slide) he did not ask me one question. The conversation only went as far as it did because I kept asking follow-up questions.

I encountered a very similar situation a few weeks ago, but this one was even worse because we had SO much in common. He was an adjunct professor, so am I. He was in a doctorate program, so am I. But despite this information being in my bio, he asked me NOTHING about any of those things.

I got so frustrated that I eventually had to say something because I felt he was acting so incredibly selfish during this conversation. This conversation should have been SO EASY for him to do well in and he couldn’t even bother to just put a “you?” behind one of his responses. Which brings me to my next point…

When in doubt, follow up with “what about you?”

Sometimes in the initial stages of a conversation, you can have a back and forth simply by just asking someone “What about you?” So many conversations could be saved this way. By not doing this ONE thing, so many conversations die.

This was during the few days of iphone hell, when the “I” was changing, but the message originally said “Ethiopia I guess.” How easy would it have been to just put a “What is your favorite place?” or “Do you like traveling?”

I borrowed another screenshot from a friend that was almost the exact same scenario:

How hard would it have been to add “Where are you thinking of vacationing?” to the end of this?!

When all else fails, don’t be afraid to change the subject

Sometimes, a conversation does just run its natural course. In the early stages, it can feel awkward abruptly changing the subject. But, sometimes this is just what you have to do. And hopefully you have swiped on someone with interesting photos and/or a good bio, and you have something else you can ask them.

For example, the other day I messaged someone something about their bio. They replied, but WITHOUT ASKING ME A QUESTION. I took the initiative to reply anyway, and they responded again without a question.

By this point, I was over the idea of replying. They weren’t asking any questions, and I really had nothing else to say about Chipotle. But, if they were interested, they could have changed the subject to something about MY profile. Sometimes we get too caught up in trying to come up with the perfect transition, but that’s not always how early conversations go.

So there you have it.

I realize this might seem like common sense to anyone not on dating apps, but I can guarantee anyone on dating apps who is even half decent at conversation finds this relatable. By just changing things in these simple ways, people would get a lot farther and might actually get to go on more dates. But until people start learning the art of a conversation (which is not even that difficult), I guess we can all tell each other how our day was.




Lover of dogs, food, coffee, bourbon, and exploring new places.