The Best Way To Start A Conversation On A Dating Site

*Sponsored by HighReply*


The dating site Highreply has compiled feedback from 20 yrs of data to find helpful insights when it comes to improving your online dating profile.

You send a message to a potential match saying, “Hey,” or “What’s Up?” and more often than not, your message is met with crickets.

An analysis of exchanges on popular dating sites conducted in 2021 by data journalist Alyssa Beatriz Fernandez shared that 57% of messages on a top dating platform are one-message conversations.

How do you make an impact on your first message that’s strong enough to get a response?

To help singles turn their dating experience from drab to fab, we’ve put together our favorite tips and openers to ensure you get a great conversation going.

Ask A Specific Question

Before contacting a potential match, be sure to read through their profile and browse through their pictures. You should be able to form a specific question from the content they shared.

From our experience and research on other dating sites, we found that shared phrases like “You mention” or “I noticed that” have a higher response rate.

Did they mention that they enjoy hiking? You can ask, “You mentioned that you like hiking. What’s been your favorite hike so far?”

Do they enjoy cooking? Perfect opportunity to ask them, “What’s your favorite dish to prepare?”

With a little effort, you can draw up questions that show you are interested in knowing more about them. Of course, asking a specific question drawn up from their shared content also indicates that you took the time to read through their profile carefully.

What Are They Looking For?

One thing that many online dating profiles need is more information on what the user is looking for in a relationship. This is pretty pertinent information required to understand whether or not someone may be a good match for you. So why not send a message asking them to share what they’re looking for? You can ask;

  • What type of relationship are you looking for?
  • Are you just looking for fun or something more serious?
  • Are you looking for a serious commitment or casual dating?

Sending this message is a great way to engage and connect on a more serious, personal level. You will be able to share what you are looking for as well. This conversation will help determine whether the discussion is worth continuing.

Some of Our Favorite Conversation Openers

Hands down, the best way to start a conversation on a dating site is to make an Impact. You can achieve this by asking unique questions that act as an Icebreaker. Try to craft questions that require a bit of thought on the responder’s part. Some of the most successful conversation openers are those that are silly and good-humored and “Would you rather” questions.

In need of a bit of inspiration? Here are some of our favorite conversation openers inspired by our most successful users on HighReply and why we love them.

What are you watching on Netflix right now?

No matter who you message, chances are they are currently enjoying a series on Netflix or other streaming platforms. Ask about what they’re watching. What’s it about? Do you like it? Are they planning on watching anything else soon?

If you had a theme song, what would it be?

This type of question is sure to get your potential match thinking and likely get back to you with something fun or witty.

If you could only eat 5 things for the rest of your life, what would they be?

This line is reserved for serious foodies. Do they mention their love for food or cooking in their profiles? Hit them with this hard-hitting question for a peek into their personality.

You’ve just won the Mega Millions lottery. What will you do with the money?

You are sure to get a peek into someone’s priorities and interests with a line like this. Will they buy a house for everyone in the family? A fleet of sports cars? Leave everything behind to travel the world?

If you could bring any 3 people — past or present — to a dinner party, who would you invite?

Yet another question that is not only hard to resist responding to, but the response gives a sneak peek into someone’s personality, allowing you to determine whether or not you two are a possible match.

I couldn’t help but notice your bookshelf. What are you reading right now?

Here is the perfect question to ask those who refer to themselves as bookworms or make a note of their reading habits. It’s a fun way to engage them in one of their biggest interests and understand the type of literature that makes them tick.

What’s your love language?

Most of us are familiar with the five love languages and which one we respond best to. So what will their love language be, affirmation, acts of service, receiving gifts, quality time, or physical touch?

Bonus Tip: How Not to Start A Conversation

By now, you know not to start a conversation with a lonely “Hey,” but there are some other things to avoid when starting a conversation. Be sure not to make these mistakes when starting a conversation on a dating site.

●      Don’t use bad grammar or broken sentences

Netspeak, bad grammar and bad spelling are turn-offs for many. This will be your first contact with a potential match – show a little effort!

●      Don’t give a compliment.

This may not seem offensive, but most compliments given on dating sites are about someone’s (usually a woman’s) physical appearance. This often feels like a lame pickup line, and you run the risk of being blown off.

●      Don’t send nude pics

Unfortunately, some people still need to be reminded of this. This happens to women way more than men would believe. Please keep your nude pics to yourself (unless someone has consented to receive them).


Dating (like a relationship) takes effort, and this includes your first conversations with a potential match. Show your genuine interest in someone by reading their profile and drafting specific questions from their shared information. Stand out from other potential suitors by thinking outside the box, opening conversations with questions that are hard to pass up, and giving the receiver a chance to share more about themselves with you. Leave the lonely “Hey” behind and start engaging in quality conversations to get things started on a positive note. Get involved in an interesting conversation at Our dating site is built with a focus on quality profiles with real individuals taking the time to make real connections. Meet others who are ready to explore their online dating options by communicating kindly and by being real.

Advertising disclosure: We may receive compensation for some of the links in our stories. Thank you for supporting the Village Voice and our advertisers.