This Is Why Your Online Dating Conversations Are Boring

Hi, I’m Amanda. Welcome to my blog, where I share online dating advice, tips, tricks, and strategies, all based on my professional training and personal experience.

One of the biggest complaints I hear about online dating is that conversations are B-O-R-I-N-G. Interactions feel superficial, pointless, and completely uninteresting. There are a few back and forth questions and comments about how the person is doing and how they spend their time, and then more often than not, it ends in one person deciding not to respond, because the conversation has stopped dead in its tracks. Most of us have had the awkward or uncomfortable in-person conversation, but there’s something unique about the experience of staring down a computer screen, having no idea how to respond to the comment someone just left, which gave you absolutely nothing to go on.

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It’s often assumed that this is just the norm in online dating. That boring conversations are just a part of the deal, and that you have to tolerate them if you want to eventually meet someone. And yet this actually doesn’t have to be the case. Boring conversations are often a sign or symptom of something else going on in the process, and if you know what the cause is, you can limit the amount of boring conversations that you have.

The cause of this usually revolves around losing sight of the point of online dating conversations in the first place, which is to decide if YOU want to go out with someone. This involves being intentional about what questions you’re asking, trying to get the most bang for your buck in the conversation, and being willing to walk away if someone isn’t a fit. Instead, online dating conversations often end up on autopilot, something to check a box on, rather than something to actively think about.

What’s the solution here? Bring more intentionality and thoughtfulness to your online dating conversations.

Without intentionality, online dating conversations can feel incredibly superficial, revolving around the weather, current events, and favorite movies and TV shows. These topics aren’t inherently bad, but if you’re hating online dating, these kinds of topics probably aren’t going to make your experience a better one. Particularly if you’re talking to multiple people at the same time, having five conversations about the weather would make anyone want to start banging their head against the wall.

A lack of intentionality can also lead to the other person steering (or not steering) the conversation, making you feel powerless in your dating experience without even realizing it. If the other person happens to be talkative, then the conversation becomes unbalanced, with the focus becoming solely on what they are looking for in a connection and whether you’re a fit for them. If they’re not talkative, then a conversation can end very quickly, without either of you really finding out anything important about the other person.

It can also make it less likely that you walk away when things clearly aren’t a fit. Autopilot typically means that you’re not tuning into the nuances of a conversation and paying attention to the data points as to whether the person is a fit for you. If these data points are there early on, that means you could end up staying in a conversation for much longer than needed with someone who isn’t a fit, which is ultimately a waste of your time and energy.

What happens when you bring intentionality to your online dating conversations?

Well, your conversations can actually be interesting. Instead of talking about the weather, you talk about things that are actually important to you. When I was dating, it was really important to me that the person was ambitious and had things in their life that they were passionate about. When I asked about that, it led to some really fun and interesting conversations, and I got to learn about things that I didn’t know much about. With my current partner, we got to geek out together on our shared music backgrounds, a topic I hadn’t been able to share with many people in a long time. It can be a great time to connect with people who have similar interests, or who can introduce you to something brand new.

Along those same lines, if I asked what the other person was passionate about, and they replied by saying nothing, it gave me very clear information that it was time to end that conversation or connection. I remember asking a match once what he did that Saturday, and when he responded by saying nothing, I responded with the somewhat smartass comment of, “Well, I assume you didn’t spend all day staring at a wall, so what did you actually DO?” Even with that, I still got the very short answer of, “I went biking.” I learned what I needed to know very early on and didn’t waste my time in a connection that was never going to go anywhere. Rather than avoiding these interactions entirely, it’s about recognizing when they’ve hit their expiration date and walking away when this happens. This way you minimize the amount of time in boring, fruitless conversations and maximize your time in interesting, productive conversations.

Finally, intentionality gives you more agency and control over how the conversations go. You’re steering the car, deciding what is important to talk about in the conversation, so that you can determine whether the person is a fit for you or not. I’ve seen a lot of women hesitant to ask the questions they want, out of fear of pushing the other person away, and yet if asking about things that are important to you makes someone want to run, then they weren’t a fit for you to begin with. This weeds out the mismatches early so that again, you’re not wasting your time.

What does it look like to bring intentionality to your online dating conversations?

First, take some time to think about what feels most important to you in your connections. What are your must haves and non-negotiables? What are your deal breakers? What are the things that you want to find out early on, so that you don’t end up wasting a lot of your time in interactions that aren’t a fit for you? Think about your values, your personality traits, the things in your life that you would be unwilling to give up for someone else.

Then think about how you want to ask about these things in a way that is appropriate for getting to know someone. When someone is scared off about a question, it’s either because 1) they weren’t a good fit, or 2) you asked it in a way that felt more like an interrogation than a getting-to-know-you conversation. If religion is important to you, then instead of saying, “I don’t date non-Christians, so tell me now if that’s you,” say something like “My faith is really important to me. Do you follow any particular faith or religion?” There are ways of asking the important questions that are very appropriate for the early stages of getting to know someone.

Lastly, don’t waste your time. If you’re putting genuine effort into trying to get to know someone, and you’re getting one-word answers in return, just move on. I set a rule for myself that if someone didn’t either ask me a question back, or at least give me a comment that I could engage with, three times in a row, I stopped engaging. I was invested in meeting someone, and I didn’t want to waste my time with people who weren’t equally as invested. I also didn’t want to waste my time with people who didn’t know how to pull their weight in a relationship. Give yourself permission to move on when things are clearly one-sided.

Online dating conversations absolutely can be boring, but they don’t have to be. By bringing intentionality and thoughtfulness to this, you can have conversations that are not only fun and interesting, but productive as well in helping you to find matches that are a good fit.

*Don’t forget to grab my free Red Flags Checklist! You’ll learn everything you need to know to scan for red flags in your swiping, conversations, and dates.

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