How to be Interesting on Online Dating Sites

woman messaging on dating site

Online dating is an incredibly popular way to meet a special someone in today’s society. In fact, it’s the most popular method of matching up with romantic interests. Dating has overwhelmingly moved to online sites, which has changed societal norms as we know them. 

Linking up with a romantic interest is far more important when you think about the implications at hand, and on a societal level. Dating leads to couples, couples lead to children, and raising children creates our future society in itself. So, naturally, society will move towards its most popular mating rituals and people will develop skillsets that support their ability to attract a partner in accordance with those rituals. 

Anthropology applies to every society, and we’re all watching our skillsets to make sure we can be a high-quality match. With the advanced popularity of online dating, these skillsets have adapted to fit the standards and specifications that online dating sites rely on. 

Anything that’s championed by an online dating site is now vital to finding romantic success. Certain skills like taking and editing an enticing and attractive photo are more important than ever before! But while an awesome profile picture will get you well on your way to finding success, you need other essential skills to get the results you’re looking for. 

So what’s the most important skill to have when it comes to online dating? The jury may be out on a few of them to win the gold, but there’s a strong argument to be made in terms of being interesting during the messaging stage of online dating. If you can be interesting while messaging someone on an online dating site, you can find a long-lasting, successful relationship that will help to form the basis of society itself. 

Now that we’ve established why it’s so important to be interesting in your messages while dating online, let’s take a deep dive into how you can go about forming and refining that skill!

Defining the Goal: What Does “Be Interesting” Look Like in Action?

Be Interesting? What is that going to help with? What results are you looking for other than finding a successful relationship at the end of the process? How will you be able to tell that your efforts are working and your skills are progressing? 

Well, even though you won’t be able to see it, you want to send the message that makes your potential match smile when they receive it. When they see your name pop up on their notifications, you want them to light up! And you’ll be able to tell this is happening by watching out for other signs of success. 

If you’re getting left on read, you’re not making the impression you want to make. If your messages are getting archived one after another, they may just not be entertaining enough. If you’re not getting left on read or archived, and your messages are getting reasonably-timed responses, your efforts are definitely getting you somewhere!

At the end of the day, messages are supposed to get you dates. Whether they’re in-person or over video chat, going on dates is the real factor that will help you determine whether or not someone is your perfect match, or if you should continue pursuing other matches. In order to figure that out, your messages have to be able to get you there. If they are leading up to dates, you’re turning being interesting into action. If your conversations tend to fizzle out before you land a date experience, there’s some room for improvement in the area of this skill!

Intention vs. Effect

It’s important to note that sometimes good intentions don’t get you the results you want to get. If you’re genuinely looking for love, you’re a better romantic prospect than many other fish in the sea. Unfortunately, that’s not enough to get you noticed if people can’t tell how authentic and amazing you are from your messages. That’s why it’s even more crucial to hone your skillset and make sure your messages are as powerful as your intentions are!

Making sure your messages are interesting and entertaining is a must if you want people to get to know you – the real you, and all of your intentions. While spicing up your messages may not seem genuine at first, it’s not manipulating your message – it’s manipulating the words you use to get your message across more effectively. Without taking the time to implement more effective messaging strategies, your intention won’t be able to get the effect it truly deserves.

It’s the same gift wrapped in different packaging. Think about going shopping for something in the store. The best product in the world could be sitting there on the shelves, but without packaging that intrigues you, you wouldn’t be likely to even notice it was there – much less pick it up and purchase it! 

Packaging matters. Interesting messaging techniques matter, too. That way, your intentions will be enabled to yield the caliber of positive effect they deserve. People will be activated and motivated to invest their emotional energy in forging a relationship with you – in other words, they’ll want to pick you up off the shelf!

Tips for How to Be Interesting While Messaging

Without further ado, let’s look at practical advice for how to improve the quality and results of your messaging on online dating sites. Check out these tips for a more playful and fun approach to messaging that’ll help you land more dates!

1. Know What Not to Say

star text messages

Being interesting and entertaining while messaging on an online dating site is as much about what you say as it is about what you don’t say. No matter how well you’re doing, if you say one very wrong thing, it’ll throw your entire conversation off course – and potentially end your relationship before it has the chance to begin. 

So before we get into any tactics that’ll be beneficial for what you’re doing, it’s extremely important to go over what not to talk about! That way, you won’t have a misunderstanding or misstep get in the way of your romantic success online. 

The most important thing to avoid is asking them how their dating life is currently going. Anything that relates to their online dating experience that doesn’t have to do with their direct contact with you shouldn’t be on the table for discussion. Not only does this kind of put you in the friend zone in a way, but they’ve also probably (sadly) already heard it before. It’s a repetitive icebreaker that people think will shine a good light on them, making them seem different from the crowd – but too many people try to set themselves apart with this question, so it ends up having the opposite effect. 

Another topic that is not up for discussion is any form of asking them why they’re currently single! This includes questions that start with a disclaimer about how they’re so wonderful you can’t imagine why they’re still single. No matter how you play it, this has an extremely high likelihood of coming off as offensive – or at the very least, unsavory. In either case, it’s not the type of effect you’re looking to have on any potential special someone. 

Asking someone how long they’ve been single or in the dating game isn’t a good strategy either. Any variation of the topics at hand probably isn’t going to work out in your favor. 

You especially want to avoid asking people how many other matches they’re currently messaging. It comes off as possessive before you’ve earned the right to be exclusive with them! The only thing people are going to see if you send that message is a red flag of someone who’s controlling or moving in way too hot and too fast – or, simply as a sign that you’re insecure, which is a notoriously unattractive trait for people in the online dating world. So even if your intention is simply to see how their online dating experience is going, this question should be avoided at all costs.

So now that you know what not to say, let’s work on what to say when you’re messaging romantic prospects online!

2. Mix Up Your Sentence Structure

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Remember in school when you had to break down sentences or write them in accordance with a certain structure? Well, what you learned in English class is about to make a comeback – and help you find the love you’re looking for online!

Even if focusing on your sentence structure might seem like the most boring way you could possibly message someone, it’s an effective way of making your messages exciting. So how does it do this? It sets you apart from everyone else by making sure you’re not saying what everyone else is saying, and how they’re saying it. It makes your messages different, giving your message the upper hand over all the generic messages in their inbox.

When you’ve read the same message a hundred and two times, a different type of message will definitely stand out – and give you that excitement you’re looking for! And the same thing goes for your matches. 

Let’s focus on your opener. How can you structure it in a unique way that’ll make your message interesting enough to capture the attention of your match and warrant a response?

Take the order of what you’d usually say in a new direction. For example, say you’re using the conventional wisdom of taking something interesting from their profile and trying to connect with them by opening with it. Instead of saying, “I see you have a dog! They’re so cute. I love dogs too!” try to mix things up a bit. Even if you say the exact same thing in a different order, it’ll be much more interesting and attention-grabbing! Try saying “I love dogs too! They’re so cute. I see you have a dog!” instead. It’s much more entertaining, isn’t it? 

Even if what you say isn’t the most entertaining sentence you could possibly muster, switching up your sentence structure will keep it new and fresh for the reader. It’ll make you stand out, as well as come off as more genuine and exciting than other online daters. So when you write a message, say what you want to say, then go back and see if you can move the structure of your sentences around. When you start to get more responses, you’ll be glad you did!

3. Keep it Short & Sweet

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If your message is too long, you risk losing the attention of the person who’s reading it! You’re not the only message in their inbox. And even if you are, you’re not the only notification on their phone, and you’re far from the only thing they’re concerned with today. People are busy, and their attention costs valuable time. And even if they’re not busy, many people would rather relax than read an actual essay from someone they haven’t even decided to date yet!

So it’s imperative to learn how to express yourself in a more succinct manner. Keeping it short and sweet is the best way to ensure someone’s going to read a message in its entirety. And if it’s too long for them to read it, you’ll be wasting your time expressing yourself with your words falling on deaf ears (or, rather, inattentive eyes). 

So if we know that longer messages might seem a little imposing or too time-consuming to read, why are they so tempting to send? Well, when we really like someone, we want to express how we’re feeling to stress the fact that we want their attention. We also want to let them get to know more about us so we’ll seem like a more attractive romantic prospect for them. 

But despite these temptations, it’s best to resist! You never want to get a TL;DR (too long, didn’t read) response – especially from someone we really want to get to know better!

The online dating world moves quickly, and one long message can make the difference between you staying in step with everyone else or you getting left behind in the chaos of rapid-fire messaging. Don’t get ditched because you have too much to say – be pickier about what you choose to divulge, and use fewer words to say it!

The goal is to keep it short & sweet – 2 or 3 lines max. If you get decent responses for a healthy amount of time, you’ll be able to ask them on a date – either in person or over video chat. Or, they might pull the trigger and ask you out instead! Either way, once you’re at that point, you’ll be in the clear to send longer messages. Make sure you already have their attention before you start sending longer messages, and you’ll be far less likely to get an adverse response from it!

4. Choose Subject Matter that Relates to Them

woman texting

Once we get into a conversation with a romantic interest, it can be tempting to talk about things we like to do – especially if we’re truly excited by the match and we want to impress them! But staying in the realm of topics you already know they like will make sure the conversation stays interesting for them. And you already have all the data you need to figure out what they want to talk about. It’s right there – in their online dating profile!

Instead of being like everyone else and trying to impress someone with your interests and hobbies, stand out from the crowd by being attentive to their interests. Read through their profile, and pull out the most interesting and message-worthy topics that you can ask them about. 

Everyone loves talking about themselves and what they love to do – so give them the opportunity! You’ll be able to get to know them, and show them you’re truly interested in them as a person and a potential romantic partner – not just their profile pictures.

Pay specific attention to the parts of their profile where they’re trying to express themselves. Focus on the more original and unusual words they use – the things they say that aren’t in every other profile you’ve read. Those are the keys to success, the topics to talk about, and the way to make your messages irresistible to answer!

After you’ve made some headway with the topics that make them special, dive into the things you’ve found that you two have in common. Focusing on common ground will help transition your conversation from a “YOU are awesome” perspective to a “WE could be awesome together” mindset – and that’s the goal!

5. Touch on Tried-and-True Topics that Stay Entertaining

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Once you’ve discussed your interests, what are you supposed to talk about?

Keeping the conversation going can be even more difficult than starting it up. And many conversations fizzle out once both parties’ interests have been divulged and discussed.

So how do you keep things interesting? 

Well, there are tried-and-true topics that have stayed notoriously entertaining over time. When the conversation slows down, time-tested topics can get you through to the next big win. And that big win might just be your first date!

We’re going to talk about two of these go-to topics that can stop you from sinking in conversation-killing quicksand: Local Life & Pop Culture. 

6. Local Life

flower drawing text messages

No matter what people are doing, they’re always living their everyday lives in the place that they live. So there’s no way to miss with this one! Instead of keeping things normal and ignorably boring like asking them how their day went, branch into how local life is in the area they’re at.

Ask about their favorite restaurant, gym, or activity site in relation to their interests. Ask where their favorite place to go with their friends is, and say you’d love to check it out sometime after they answer!

Since these answers can be a bit more personal, we kept this one for a little later in the conversation. Questions about local life aren’t openers – that can come off as stalker-ish at best! So be tactful and tasteful with these questions – but remember there are plenty to ask. So if the conversation lulls, you can easily dig into something they love and embrace on a regular basis by focusing on how local life is. And, the bonus here is that you get a picture about what it’d be like to visit them or spend a day with them if you two were to get into a relationship!

7. Pop Culture

colorful flower text messages

When it comes to pop culture, you really can’t miss – you just have to ask them what they like! While this can be a boring opener and seem cookie-cutter early on in the conversation when you’ve got a few messages and some time in, pop culture can be the perfect topic. 

Once you’ve got someone’s attention and interest, they’ll be more likely to really love opening up to you about what they love in pop culture. And when people love movies, music, or tv shows, they tend to really love it – and love talking about it!

Also – is there something new on tv or your favorite streaming site that you think they’d be into based on what you already know they like? Mention it! It can be an amazing thing to bond over – and maybe even set you up for a video date where you can stream it together. Is a new movie coming out? Dinner and a movie is a great classic date to take someone on. Pop culture topics can be the best segway to your first date if you do your due diligence and pick something they’ll love!

8. Get Flirty

flower text message

While you don’t want to ever seem aggressive or crass, at the end of the day, you are dating! And since online dating is, in fact, dating, you have every right to get flirty in a respectful way.

We recommend starting in with compliments and flirtatious comments later in the conversation after you’ve earned their attention, interest, and respect. That way, your advances will be far more likely to be welcome, and won’t have a high probability of scaring off your potential partner. 

People want to know that they’re liked for who they are, not just what they look like in the pictures they’ve posted. Once they have an understanding of that through some meaningful and entertaining conversation, it’s time to tap into the chemistry. If you don’t start flirting at that point, you run the risk of being friend-zoned. Keeping it romantically interesting is the most important thing after a bit of time.

So give them a few compliments! Try to stick to one or two of them per conversation so you’re not laying it on too thick. And try to make them genuine and respectful – you don’t want to come out of the blue focusing on body parts that they may not be entirely comfortable discussing with you yet. Smiles and fashion sense are always good options! And they don’t have to be physical in nature, either – being kind and having a sense of humor are also on the board!

Once you’ve put in a little work, don’t be afraid to flirt! Have fun with it. If they weren’t interested in dating you, they wouldn’t be talking to you in the first place. So make sure you’re on the same page by revving their engine by spicing up the conversation a little bit. Note – save deep romantic professions for later – you’re not there yet! But letting them know why you’re romantically interested in them will keep your budding relationship on the perfect track. 

9. Get Hypothetical

man texting

When you want to make the conversation a little more fun, it’s time to break out the hypotheticals! After you’ve already touched upon everything real life and pop culture has to offer, you can feel like you’re looking at a conversational brick wall. But there are fun, fake scenarios that’ll show you another stretch of road to take. And when you’re messaging in a conversation on an online dating site and intentionally keeping it interesting, the only thing you need to know is where to go next!

Whether you come up with your own or find some hypothetical questions through an internet search, there are plenty of things that you and your potential romantic partner can consider together. Good starting points are usually “Would you rather” or “What would you do if”. 

Not only are hypothetical questions entertaining – they’re thought-provoking! They allow you to get to know your match on a better, different level – and might even let you get to know yourself a little better as well! I mean, how would you try to survive a zombie apocalypse?


Being interesting during the messaging phase of your online dating relationships will take you all the way to your first date! It’ll keep your romantic match engaged and entertained through the courting process, ensuring you get a shot at a real relationship. Whether or not you end up being entirely compatible with each match you talk to (which you probably won’t) having the skill of keeping your messaging interactions captivating will up your odds of finding the true love you’re looking for. 

Set yourself up for success by taking note of these tips! By focusing on what you talk about, how you present that information, and when you bring up certain entertaining topics of discussion, you’ll be following a roadmap that leads you to your best possible outcome. Do this with every match you’re interested in, and given time you’ll land on the right person for you!

Thank you for reading – we hope these tips help you to make a meaningful connection with you’re looking for love online!

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