Matching with someone on dating apps is the easy part; turning a silent match into a genuine chat is where most people get stuck. Staring at a blank message box with only a handful of holiday photos and a three-line bio to go on can make even confident talkers freeze up.
Once you make that initial connection, the focus moves firmly to the conversation. When you are chatting online, there is nothing you can both fall back on as a background distraction. It is not like meeting someone in a pub or bar where music, a busy room or buying the next round can naturally fill the gaps. An online conversation on a dating site needs a bit of rhythm, otherwise it quickly feels stunted and awkward. Here is our practical advice on how to get a chat moving and keep it flowing smoothly.
Key takeaways
- Anchor your first message to a specific detail in their photos or bio rather than sending a generic greeting.
- Keep messages to a single phone screen and finish with an easy, open question to share the conversational load.
- Send one complete thought at a time instead of firing off six rapid-fire notifications in a row.
- Leave out premature pet names, explicit talk and complaints about your ex or how much you dislike online dating.
- When a topic naturally winds down, pivot to a fresh thread or suggest a relaxed drink or coffee in person.
Contents
1. Start with an Ice Breaker
A great online conversation starts with a thoughtful opener. Base your first message on the other person’s profile rather than firing off a generic “Hey, how was your weekend?” Take thirty seconds to actually read what they have written and look properly at their photos so you can pick out a detail worth talking about.
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 counts just as much for online dating as it does for meeting in person. When you are chatting with someone new, take a moment to write clearly using decent spelling and punctuation. Nobody expects an academic essay (see the next point for more on that), but walls of sloppy “text speak” are tiring to decode and make it look as though you cannot quite be bothered.
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 hit 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 down to Cornwall on summer holidays. It was always such fine weather and we spent 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 and it was an absolute disaster. She made my life miserable for six months, so I can’t say I’m very optimistic about being back on here…
Grumbling about how long you have been single or how rarely online dating works for you puts your match in an awkward spot before you have even met. Instead of sounding candid, it tends to come across as jaded and heavy—which quickly becomes a self-fulfilling prophecy.
Red flags
- Opening with a one-word “Hey” or jumping straight to “babe” and sexual comments.
- Sending six separate notifications to express a single thought, or writing a multi-paragraph life story.
- Answering questions without ever asking anything back, leaving the other person to carry the chat.
- Using early messages to vent about an ex or complain about how awful dating apps are.
Green flags
- Picking up on a specific detail from their photos or prompts to start a natural conversation.
- Keeping replies to a comfortable screenful and ending with an easy question for them to answer.
- Matching their tone with light, good-natured humour rather than heavy oversharing.
- Pivoting smoothly to a new topic or suggesting a coffee when the back-and-forth is flowing well.
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.
A simple bridge is all you need when a subject has run its course. You can pick up on another clue from their profile or try a relaxed pivot such as: “Before I get us completely sidetracked by travel stories—what does a good Sunday usually look like for you?” And if you have already looped through two or three topics with warm, prompt replies from both sides, take that as your cue to move things offline. You do not need weeks of pen-pal messaging; a simple “I’m really enjoying this chat—fancy continuing it over a coffee or a drink this week?” is often the best next step.
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.
