Dating guides and tips

How to Have a Conversation on a Dating Site

Online dating platforms have moved at a lightning pace from the fringes of the dating world firmly into the mainstream. Dating apps and other platforms have established themselves as people’s favourite way to connect. A 2019 study from sociologist Michael Rosenfeld at Stanford University has found that it is already the case that heterosexual couples are more likely to meet a romantic partner online than through any other channel.

When you make that initial connection online, the focus then moves firmly to the conversation. When you’re chatting online or via SMS text message, there’s nothing that you can both fall back on as a background distraction. It’s not like when you meet someone at a bar and you can allow music or dancing to fill in the conversation gaps. An online conversation on a dating site needs to flow, otherwise it quickly feels stunted and awkward. In today’s blog, we’ll be offering our best advice on how to keep your online conversation going smoothly.

1. Start with an Ice Breaker

A great online conversation always starts with an ice breaker. You should base your first message on the other person’s profile information, so you will have to a little intelligence gathering, possibly a little inference and cold reading too based on the given profile information.

Check the bio and photos for the best clues. Let’s say, for instance, that you find a collection of photos of different travel destinations, you might start with a simple:

“Wow, it looks like you’ve seen a lot of the world! What was your favourite destination?”

This ice-breaker works on many levels. First of all, it’s not sexual or off-putting (see point 6 for more on that). Second, it expresses an interest in something about the other person, which is always nice. Third, it gives an easy-going and natural framework upon which the other person can reply to you.

Perhaps with the traveller scenario, you’re also someone who has travelled widely and you spot a photo of a place you also visited. It’s a good chance to inject a little humour into the ice breaker.

“Ah, a fellow traveller! Tell me, what was your favourite destination and why was it Australia? 😉

Getting a little giggle from your new love interest isn’t a bad way to kick things off.

2. Ask Questions

As the conversation gets going, it requires fuel to maintain its momentum. The best fuel to provide the conversation is questions. Each time you reply to their question, add something of your own, even if it’s just a simple, “and you?” The humble question is the oxygen that keeps the romantic fires of the conversation alive.

The more questions that roll in, the longer the conversation goes and the more you learn about the other person. The other positive effect of maintaining the conversation with questions, of course, is that sooner or later one of those questions could concern setting up a real face-to-face meet-up and date.

If one line of questioning seems to go a bit dry, don’t be afraid to change the subject (see point 8 for more). You can use the other person’s photo or bio information as prompts for further topics. Be aware of the conversation becoming too one-sided, as well. If it’s you asking all the questions, then things aren’t progressing in a positive way. That’s a sign that they’re perhaps not as interested in you as you are in them.

3. Write Properly

The rule about only getting one first impression with someone counts just as much for online dating as it does for in-person meetings. When you’re having a conversation with someone, try to write properly using correct spelling, syntax and grammar. We’re not saying write an essay (see next point for more on that one), but lazy “text speak” is tiresome and conveys a lack of intelligence.

The abbreviated language of the 2000s Nokia 3300 SMS text message world is a thing of the past. Typing on smartphones is much easier than it was when you had to his that number button three or even four times to get just one letter that you wanted. Write properly and make a good impression.

4. Avoid Rambling Messages

To keep the flow of the conversation, avoid essay-like messages that go on and on before they finally come to the point. It should fit well within one screen and finish with a neat question or inquiry to allow the other person to feel comfortable replying with ease. Here’s an example.

Them: So, if you had an entirely free week, what would you do with that time?

You: For me it has to be the beach or just anywhere coastal. I love the ocean scenery, beach barbecue, surfing, the whole scene. How about you?

This answer has thoughtful details about yourself while also being short enough to enjoy, and ending on a question for your new interest to answer. Most importantly, it isn’t long and rambling.

You: Well, it’s funny you should mention having a week off. That takes me back to my childhood when my family and I would head out to Cape Cod on summer vacations. It was always such fine weather and we spend literally hours…

…slow down, Casanova. Save some story for your second date!

5. Don’t “Fragment” the Messages

On the flipside of long and seemingly endless messages are those ones that are unnecessarily broken into a million pieces. You might think you’re keeping the messages short and sweet, but all the other person gets is the “ping, ping, ping!” of endless message notifications. It can actually make things quite awkward.

Them: I visited Aspen last year with some friends and had an amazing time. Do you like to ski too?

You: Oh sure

You: It’s great

You: Never been to Aspen though

You: Went to Whistler a few years back

You: That place is great

You: Just…

You: …Awesome!

Many people who fragment messages like this think nothing of it, but it can easily be off-putting for the other person who can feel bombarded by your many unnecessary messages. Get all you need into one message, not too long, and with that all-important and inviting question at the end.

6. Leave Out the Sexting and Pet Names (But Don’t Be Afraid of Flirtation)

Another key point is to avoid using pet names like “babe” or “sexy” when you’re just starting a conversation. If you want to make a real connection with someone and build to something meaningful, you should avoid sex talk and familiar pet names entirely in your initial chat. You hardly know them, and you just risk crossing all kinds of red lines.

None of this is to say that a little bit of mild flirtation has no place in the conversation. If the ice breaker seems to have been taken very positively and you are well engaged in a conversation, there’s nothing wrong with spicing up the questions just a little with some tongue-in-cheek flirtation. One interesting approach is to add a little “sass” into the conversation.

You: A cat person, really? Come on now, everyone knows that dog lovers make for better boyfriends 😉

Nothing has to become overt, and the conversation doesn’t have to go anywhere beyond that fun flirty foundation. It can be a fun way to keep the conversation engaging and flowing.

7. Be Positive

Another killer to online conversations is negativity. Have you ever started a conversation talking about how much you hate online dating? Maybe you opened up with talking about how long you’ve been single or how much you hate your ex? None of this negative talk is conducive to forming a good connection. The best policy is to stay positive.

Them: You done much online dating?

You: Sure, I’ve used these platforms before. They’re always a way to meet interesting people! I’m still single at the moment but always hopeful. How about you?

Them: I met my last girlfriend online. She turned out to be a total b**ch troll from hell who was sent to Earth to make my life miserable. Can’t say I’m so optimistic about this kind of platform…

To be negative talking about, for example, how long you’ve been trying (without success) at online dating is like you’re advertising the fact that you’re dating anyone and everyone and being a real downer all the time. It can actually be a kind of vicious cycle.

8. Don’t Be Afraid to Change the Subject When Needed

Finally, when one point of conversation seems to be wrapping itself up, don’t be afraid to “refresh” the conversation with a new question. Don’t think of the online dating app conversation like that of a single linear progression. It’s actually more of a loop-de-loop. It begins with one of those ice-breaker like conversation starters, then evolves into a mini dialogue in which you learn a few things about each other, and then you go back to the beginning and start again.

Some conversations run dry simply because one party is afraid that they have “run out of things to say.” If one party is bold enough to start a fresh line of inquiry, then all that same positivity and mutual understanding starts to flow once more.

Let the Conversation Flow

One of the best things about online conversation is that it can be a good indicator as to whether you have a real connection with a person. Chatting someone up in a bar where everyone is fuelled by alcohol (or worse) can give a kind of “false reading” on your connection with another person. If you can keep an online conversation interesting and flowing over a day, or even a few days, then the grounds for a real relationship are actually a lot stronger.

Try out the things we’ve said above in your next online conversation and see if it doesn’t improve the flow and quality of your dialogue. Be bold, but don’t cross the line; be flirtatious, but not seedy; ask and answer questions with interesting details, but don’t ramble. It’s actually a lot easier than you imagine.