The Only Tips for Online Dating Conversations You’ll Ever Need

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how can you start an online dating conversation? Here are some tips to help you kick off a chat with the perfect match.

In a perfect world, your future husband would be having dinner with a mutual friend at a restaurant. You’d walk in to have dinner with your friends and notice them. The mutual friend would then introduce you to his friend, and he’d shake your hand, saying, “I like you.”

Throughout the rest of dinner, he would just stand there and make you laugh. But sorry, friends, you’re not as lucky as Emily Blunt and John Krasinski.

Finding a partner in such a scenario is hard in real life—it’s like a fairy tale. Instead, people are connecting through online dating apps. Over 40 million users are using online dating services in the United States. As a result, the chance of finding love is at its peak. 

But, to enjoy these services, you need to know how to have online dating conversations. This article will teach you all the valuable tips for online dating conversations.

But first…

What is online dating?

Online dating is a way of meeting people through the internet for them to find potential romantic partners. With the advancements in technology, you can use your phone or computer to access an online dating app or website to meet a potential partner.

You can sign up on different online dating sites or apps by creating a profile. You need a picture of yourself, a brief description, and matching preferences. 

Online dating services use software to provide you with matches of potential partners based on algorithms that match a user with other users based on the information provided.

There are different online dating apps and sites; Tinder, Bumble, OkCupid, Match, Grindr, etc. Some sites focus on matching people with a specific interest and preference; others on age group, sexuality, religious background, hobbies, etc. 

A man starting the tinder app on his iPhone
A man starting the tinder app on his iPhone.

The benefits of online dating

Why should you try online dating? Well, here are some great reasons why you should give it a shot if you’re single.

It increases the chance of a potential partner

There are millions of people using online dating services. The apps and sites allow you to swipe through thousands of people until you find your match. Additionally, every day you’ll keep getting suggestions for new matches.

Then, you can talk to your matches to get to know them and assess the degree of compatibility. You can use filters to find the kind of people you’re looking for, removing uncertainty about specific issues such as religion, age, gender, and so much more.

It gives you a chance to date beyond your location

When you join an online dating site, your profile can be visible to people worldwide. These apps and sites make it possible to date away from your city, state, and country. You can be in New York and be talking to someone in Canada. Also, if you decide to move from your current location, you can change that on the site.

It allows you to date at your own pace

If you’ve been single for a long time, online dating allows you to move at your own pace. No hurry, no pressure. It is a great option even if you just want someone to talk to and are not ready for a face-to-face meeting.

It makes it easy to vet your date

Online dating is very efficient. Online apps and sites have a chat feature that allows you to ask questions and interact with other people. 

This feature allows you to get a feel of what their personality is like.

Other sites have introduced video technology that allows you to have a virtual date to get a glimpse of their personality. This minimizes the chance of meeting the person in real life and realizing that they are the complete opposite of what you thought.

Woman using dating app on a laptop
Woman using dating app on a laptop.

It is suitable for shy people

For shy and introverted people who have a problem speaking with strangers, this option might help. You can talk to as many people as possible while building a connection. 

If you get lucky and establish a genuine connection, meeting them in real life might be easy because they don’t feel like strangers.

Disadvantages of online dating

As much as there are benefits to online dating, there are also drawbacks. Let’s check out some of them below.

  • The algorithms might not always work perfectly.
  • You don’t know the other person’s intention.
  • Some people might create fake profiles.
  • It could be dangerous: insults, trolling, catfishing, etc.
  • You could receive unwanted sexual messages.
  • People can lie on their profiles.

How to start an online dating conversation

So, you have a couple of matches, and you’re nervous about sending the first message because the normal “hey, how are you?” message might go unanswered. As a matter of fact, a 2021 analysis of Tinder conversations shows that 57% of the first messages go unanswered. 

So, how can you start an online dating conversation? Here are some tips to help you kick off a chat with the perfect match.

How to start an online dating conversation

Ask about something that stands out on their profile

As you go through their profile, scan it for some hints, clues, or statements you could use to send a message. You could ask a question or make fun of something they’ve posted or said. 

For instance, if there’s a “foodie alert” on the profile, you could share something funny and witty or ask a question about food.

Example: “I noticed that you love food. How do you like your pizza? Thick or thin crust?” or “Wow. I have never skydived before. How was your experience?”

This tactic shows them that you took the time to check their profile. People like being noticed; it makes them feel heard and shows that you genuinely like them.

Ask open-ended questions

“What’s one thing people assume about you that isn’t necessarily true?”

Open-ended questions provide you with a chance to get to know a little bit about them. They can give information about their family, work, interests, relationships with friends, etc. 

Many people only briefly describe who they are on their profile. By asking questions, you give them a chance to let them talk about themselves.

Chances are the other person would want to give you a little information and ask you questions as well, which shows they’re interested in getting to know you.

Get a game going

Playing games can be a good way to avoid small talk and boring first conversations. You can ask a “would you rather” to get a glimpse of their personality. 

For example, “would you rather oversleep every day for a week or not get any sleep for three days?” or “Would you rather stay indoors and chill over the weekend or go partying with friends?”

This is a fun and creative way to get to know them. You can also play “two truths and a lie.”

Write two truths about yourself and a lie, and have them guess which is which.

Share experiences

If you’re both living in the same location, you could use this information to share your experiences. 

“Hey, I just visited Kyle Field last weekend. It was amazing. Have you been there yet?”

“What’s your favorite and least favorite part about fall in New York?”

Alternatively, you could ask how their experience on the site has been and exchange the weirdest opening lines you’ve both received.

A shared experience can create a great conversation. 

Use a cheesy pick-up line

Cheesy pick-up lines could work like a charm if you can’t find the right words to say. They can make your match smile a little, roll their eyes, and will probably answer you back.

“Apart from being sexy, what else do you do for a living?”

Tips to keep an online conversation going?

Woman reading chats on a dating app
Woman reading chats on a dating app.

So, you’re past the first awkward message, and they’ve replied. Good for you. 

But what’s next?

It’s hard to keep an online conversation going, and no one likes that awkward pause after the initial exchange. You want to keep it flowing and come off as smart, serious, funny, interesting, and flirty. How can you accomplish that?

Here are some tips for keeping an online conversation going.

  • Ask more open-ended questions.
  • Tell them to share something about themselves, e.g., their favorite food, music, etc.
  • Talk about your favorite subjects, but keep it light and fun.
  • Send memes or jokes.
  • Check your last conversation and see if you can ask a follow-up question about something specific.
  • Be a little flirty.


Well, there you go, ladies and gentlemen. Online dating can be where you meet your future husband or wife. We don’t want you to mess it up with the cliches. Put these tips to test and wow your matches. 

Before you know it, the chat starts flowing smoothly and the two of you get along wonderfully.

So, are you ready for love? Let’s go!

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Over the years, Stephanie has had her fair share of dating experiences. While some turned out great, others weren't so great. She believes that relationships are meant to be fun, exciting, and full of laughter. She wants to help men and women become confident, attractive, and successful in their romantic relationships.