How to Start a Conversation with a Guy Online

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Most people consider themselves to be great conversationalists. However, when you are faced with the idea of starting a conversation with a guy that you like, the task can be daunting. Often, you can start to overthink and end up choosing a boring way making your matches on free dating sites lose interest quickly. You may also be missing out on opportunities for second dates because of how you text.

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Ideally, you want to have engaging, intriguing, and funny texts guaranteeing he will text you back. The texts should keep him interested, and it should be totally different from how you chat with your friends. We will look at a few tips you can follow when starting a conversation with a guy. Let’s get started.

Make the Text Interesting

“Hey, how are you?” Is this how you have been starting your conversations once you find a match on a dating website? Don’t do that!It is generic, boring, and closed.

Often, starting a conversation that is unlikely to receive a response. You will have many opportunities to discuss how they are and if he is okay once you get to know them. Your goal when texting him should be to make the message intriguing enough to get a response immediately if he is online.

Instead of tired, worn out and dull phrases, look at their dating profile to find a personal thing to use as a way in. If this is the cute guy you see every day and all you do is say hi in passing, you need to think about something personal that you may have noticed about them. If you have exchanged a few words, use the information when starting the conversation. It will show him that you are a good listener or that you are observant.

However, be very careful not to appear like a stalker. If you have gone overboard and looked at his social media pages to know when he first posts appeared, this is not the time to use that information. It can give him the impression that you are a bit nuts. You clearly don’t want that.

Use a Meme or a Gif


If you have a sense of humor, this is a tactic that you can use. Find a meme that is funny and relevant to make him laugh. Guys love girls who can make them laugh. Since it’s trendy, sending a meme to a guy you like does not appear desperate, and it makes for an exciting conversation starter. You can send a catchy caption to go with the meme. If the meme is based on something you discussed when on a date, it might remind him he had such a great time with you. It can lead to a second date and many more.

If you have an inside joke, it is the best time to apply this information. It is a nice way of knowing how you can gently tease each other and keeping things light. A gif makes for a great icebreaker. If that’s the first message on the dating site after a match, you can use a cheeky meme guaranteeing a reply.

However, when using humor to start a conversation, you need to know how to express the jokes on texts to avoid misinterpretation. Make use of the emojis sufficiently; otherwise, a sarcastic and witty reply may be interpreted as bitchy or nasty. Triple-check your message making sure they cannot ruin your chances.

Open Questions

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Do you want that cute guy to reply to your message? You should avoid closed messages. He may struggle to come up with a reply or a follow-up with the conversation, making leaving your message on reading. Make the Experience easy for him by including questions from the first message to the ones that follow.

Ideally, the goal is to have an engaging conversation. So, when asking these questions, you need to avoid using generic messages too. You can ask the questions referencing earlier events. If he had mentioned plans about going to an event, you could make the question about that.

However, when asking questions, remember that too many questions can be overwhelming. As a result, he can pull away or lose interest in the conversation. It should be a free-flowing conversation void of interrogation.

Using His Name

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Do you want to grab his attention and engage with him? Use his name. Using someone’s name in a text makes it easy to start a conversation. It acknowledges his identity and makes the conversation feel more personal. We have been conditioned to pay attention when our names are mentioned from an early age.

Using that name in the first message after getting a match on top dating sites will register subconsciously, making him pay attention. As a result, you will receive a very quick response. Though it’s a tried and tested method, do not overdo it. It may appear weird or downright manipulative.

Ask Questions About Him

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Now that you know how to start a conversation, you need to know the content that will keep the conversation flowing. You can get even the silent types to engage with you by talking about them. Asking open-ended questions regarding topics that interest him will get you a long comfortable conversation. He will find the conversation to be more interesting when it is centered around him.

You start with things that you have in common as you progress to new topics as he brings them up. Look for opportunities of connecting topics with previous information naturally. This is a trick that makes you appear like a good conversationalist and confident.

When starting a conversation, remember to keep it light and friendly. As you ask questions about him, do not make it too personal. Avoid questions about his past relationships or sexual history. It can make this first interaction too awkward. As you get to know each other, you will naturally flow into those topics.

Ask Him for an Opinion or Recommendation

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Have you gone through his profile on an online dating app and seen that he likes a particular restaurant you have been dying to try out? This information makes for a great icebreaker. People enjoy giving a recommendation. You can ask, ‘Hey, (name) I see you have been to (the name of the restaurant). I have been dying to try it out. In your opinion is it worth the hype?’

From that simple message, the conversation will take a life of its own. If you share the same music interests, you can ask them to recommend a new album. You can also follow up with your own recommendations. This type of banter can cover all the topics you have in common.

Refer to Pop Culture

If his profile reads, he loves comedy; this is your time to make those corny references; whether you want to use a famous line from ‘The office” or sign out that funny meme with ‘Bazinga,’ you can go all out. Going the Friends show the way and asking if Ross and Rachel were on a break. You never know what that reference might uncover.


Be Confident

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When you are texting him first, you are making the first move. Whether you met him at a pub, and he gave you his number because his phone’s battery had died, or he was the recommended match on top free dating sites, you will need to show your interest. When doing so, you need to be confident in this decision. The modern woman is unafraid when it comes to wooing the man of her dreams.

If there is a connection, you can willingly bypass the three-day rule. However, don’t be a Ted Mosby (a character in How I Met Your Mother show). You do not want to declare your undying love after the first date. If you’re going to ask him for a second date, do not come on too strong, as it can squash your chances of having a second date.

Notice All the Queues

When interacting with people, what they say is as important as how they say. Sometimes, how they say something is much more important. These non-verbal cues guide our interactions. Since it’s considered rude to say what we think outrightly, our body language compensates by doing the exact opposite of what we are saying.

The voice can gain a lilt when talking about something we are excited about. When chatting, if he is engaged in the conversation, he replies to all the messages quickly. They may also type a bit faster. As you chat on a dating app, you may notice he is flirty and genuinely engaged; it shows he likes the conversation. Therefore, you can keep the conversation going.

If they start losing interest, they can take time to reply to the messages. You can also receive terse or one-word replies. It can be a cue for you to change the topic by talking about their interests.

Don’t Double Text

How to start a chat on a dating app

If he leaves your text on reading, it can be tempting for you to send him other texts to prompt him. This is not a wise move. We’ve all been there where we have sent someone a text after blue ticks. It doesn’t feel good.

There are genuine and good reasons why he may not be texting back. It can be a family emergency or too busy at work. You need to give him space to reply. When he replies to you during his own time, he will appreciate that you did not rush him, which will work in your favor.

If it takes several days before hearing from him again, it could mean he is not feeling it, or he may have found another fantastic date. It may be hard to listen to this; however, swallow your pride and get back to looking for other potential mates on free dating websites. Texting frequently without replies might make you appear a bit crazy.

Text when You have Time

Have you received those daily matches from a free dating site and seen a guy you like? You may be eager to start a conversation with them immediately because you can see they are still online. However, do not do it if you do not have time on your hands. If you do so and take too long between replies, he may lose interest in you and start texting another woman.

Also, when you find that perfect conversational starter and he replies, do not take long replying to the messages. Besides, if you already bent the social rules to texting him first, you cannot play the game. Although you may choose to wait before you text immediately, you do not want him to assume you are ignoring him by taking hours before you reply.

It is an important point to remember, especially if they can see when you were last online. If they see this information, they will know you are ignoring them, which does not make for a good first impression.

Instead of playing games, ensure you text him back the next time you look at your phone. Also, stay calm and relaxed throughout the interaction. It will make you come across as confident and sure of what you want.


Even if the relationship doesn’t materialize out of the conversation, you start to practice how well you can have a conversation with a guy and keep him engaged. Like with any other skill, it becomes better with time. The more you practice, the better you get. You can follow the same tips when chatting with a guy you’ve just met. Remember to be confident and keep the conversation light and engaging. You cannot go wrong when you make it about them.

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