If you’ve found a dating app that feels right for you and have set up your dating profile, the next step is finding possible matches and starting a conversation (or two). Your first contact is a really important part of the process and will help you get off to a positive start on your dating journey.
But how do you open a conversation without sounding too keen, not keen enough, even cheesy or bland? Below, we share our top tips on starting a conversation on a dating app along with expert advice from sex and relationship coach, Angela Vossen.
If you have found someone you think you would be compatible with and want to get to know them better, take a close look at their dating profile before messaging them directly. Then keep things friendly and light while making any questions you ask open-ended ones. Sharing something about yourself will also make the recipient feel more comfortable sharing things with you too.
No less importantly, what should you avoid saying? Don’t focus solely on how your match looks in their profile photo. While attraction is important and compliments are nice, it’s far from the only factor that matters and focusing only on a person’s looks may come across as shallow.
Once you have sent an initial message, try to maintain a good conversation. “Think of it less like performing and more like opening a door and leaving it ajar,” says Angela. “You’re not auditioning; you’re inviting. And the goal isn’t to dazzle; it’s to make replying feel easy and natural.”
She adds that good conversation has a rhythm of give and take, so ask questions out of genuine curiosity rather than firing them off like it’s a job interview. And share something of yourself too.
“Reciprocity is what turns an exchange into an actual connection,” she says. “And remember: timing and responsiveness matter just as much as what you say. Conversations fade not always because someone lost interest, but because someone lost attentiveness. If you’re taking 24 hours to reply, you’re essentially sending a carrier pigeon instead of a message. Show up. Presence is part of the seduction.”
Taking the time to read someone’s dating bio and profile information will help you lead with genuine questions and get the conversation off to a good start. Try not to get too personal too quickly, though. For instance, if their profile states that they are a widow or are divorced, don’t lead the conversation with questions about this. Sensitive subjects are better discussed in person when you have got to know one another better.
The dating profile of a potential match should have lots of key information, such as their hobbies, interests and photos. Use these nuggets of information to ask questions and start a genuine conversation. ‘I see you’re a keen runner and go to regular park runs. So do I,’ shows genuine interest while offering detail about yourself too. You could also ask them questions about photos they have shared on the app or something simple such as how their weekend was.
Starting a conversation with a very generic opening line such as ‘Hey, how are you?’ or just ‘Hello’ leaves the work of starting the conversation to the other person. Instead, lead with something more specific such as a warm introduction and an explanation as to why their profile stood out to you.
You can then ask a question that is specific to your match, such as, ‘I see from your profile that you’ve travelled a lot. Where did you go on your last trip? I recently got back from two weeks in France.’ In this example, you’re showing interest in them without asking anything too intrusive, and sharing more detail about your own life.
Humour can be a great way of breaking the ice when used in the right way. For instance, you could say something playful such as, ‘I saw your profile and it looks like you’re a tennis player too. Maybe we should plan a game and see who has the better backhand?’ Alternatively, lead with something such as ‘I’m new to online dating. How are you finding it? Hopefully it’s about to get a lot better.’
Be mindful of being too sarcastic or dry initially as this may not always translate well over text or direct message. Humour such as this is best left until you have met in person and become more acquainted with each other’s tone and personality.
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Open-ended questions encourage deeper conversation and allow the conversation to flow more naturally. Here are a few examples that will help you to get to know each other better:
“This or that?” questions can be a really fun way of getting to know someone and are ideal for first dates or getting the conversation started. Take it in turns to answer questions such as ‘tea or coffee?’, ‘beach or mountains?’, ‘cats or dogs?’, ‘podcast or playlist?’ or ‘stay in or go out?’. The options are countless.
Additionally, ‘this or that?’ questions will also bring up lots of different discussion topics too where you can expand further on your answers. For instance, if you chose mountains over a beach, you can explain more about why this is. Perhaps you went on an unforgettable hike that you would love to share more about. You could even use this game to decide where you go on your next date.
Questions such as ‘romantic dinner or active adventure?’ for instance, will make your dating experience fun and reciprocal.
Sharing a fun fact about yourself allows you to get more personal in a light-hearted way. This keeps the initial stages of conversation authentic without getting on to topics such as past relationships that may be too serious. This could be anything from a hidden talent to something unusual that happened to you such as meeting a film star or appearing on TV.
Being playful and asking fun questions is a great way of getting to know someone new. Asking further follow-up questions about a light-hearted answer they have given shows genuine interest and a willingness to know more about them.
If you’re sensing that the person you’re messaging is losing interest on a certain topic, don’t be afraid to shift the conversation to something else. We all have hobbies and areas of interest that we’re passionate about, but it’s important to know when to change course. Have they started answering more briefly or less frequently? Ask them something about themselves to get the conversation flowing again.
If you feel the need to move to a new topic of conversation, try and do this subtly and naturally. Saying something such as ‘On a completely different topic…’ before changing tack keeps things flowing without the chat grinding to a halt. If you feel you’ve overshared too early and sensed the other person feels uncomfortable, move on gently by saying, ‘on a lighter note…’ or ‘that’s enough about me. I’d love to know more about you.’
If you’ve been messaging frequently with a potential match and you feel that the interest is one-sided or they won’t commit to meeting in person, take note of this and don’t force it. There is no harm in making your intentions clear (such as that you would love to meet for a coffee etc) but if they don’t reciprocate or are vague in their response, place your focus on making other connections.
If things aren’t going well (perhaps the conversation has started to slow or even made you feel uncomfortable), it’s absolutely fine to leave. The graceful way to do this is by thanking them for the chat and wishing them all the best in their dating journey. This makes it clear you’re moving on without being rude or leaving them feeling ghosted.
Likewise, if you want to keep the door ajar to a slow responder, write something such as ‘let me know if you ever fancy grabbing that coffee’ before leaving the conversation. This allows you to preserve your dignity without completely shutting down a potential connection.
Why is this important? Angela explains that not every faded thread is a rejection. “Sometimes it's just someone who got busy and felt too awkward to re-engage,” she says. Ending with a comment like this leaves the ball in their court and doesn’t sound rude or dismissive.
No one likes to feel as if they are just another number in someone’s dating experience, so avoid sending generic and impersonal messages. You may think it’s a good idea to send ‘Hi, how are you?’ messages to lots of different people, but low-effort greetings such as this may not inspire the recipient to reply and engage further.
Angela says that asking for a connection’s number before you’ve established any real chemistry or commenting solely on their appearance are two common ways of being overly forward on dating apps. Both can seem arrogant and shallow and may be off-putting to a potential match.
Try not to send multiple messages before the recipient has had a chance to reply to one. Receiving a barrage of messages from someone they don’t know can come across as overly intense and place unnecessary pressure on a new connection.
Complaining, being overly negative or so self-deprecating that it becomes a burden for a potential match to carry are all key things to avoid on dating apps. Try to keep the chat upbeat, positive and fun.
For more dating advice, head to Telegraph Media Group’s dating hub. If you’re single and interested in meeting like-minded people, join Telegraph Dating. With more than 220,000 single people, Telegraph Dating is the perfect place to find romance.
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