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How to Keep a Conversation Going with a Guy: 20 Ways To Connect 24/7

When it comes to knowing how to keep a conversation going with a guy, it’s really not that complicated. Be yourself, and the rest should follow!

how to keep a conversation going with a guy

Talking to someone new isn’t always easy, especially when you have a crush on them. Figuring out how to keep a conversation going with a guy you are crushing on can feel overwhelming! You spend so much time trying to figure out what to say, if they like you, or want to see you in person.

[Read: How to keep a conversation going with just about anyone you talk to!]

But it’s really as easy as riding a bike! Especially since most of our conversations happen either on texts or online, it makes things easier *rather than dealing with the inevitable pain of awkward face-to-face conversations*. [Read: Texting anxiety – How to send and receive texts without freaking out]

How to keep a conversation going with a guy

We understand entirely the nerves talking to someone new can bring up. If you’re talking to him via text, it’s a little easier in some ways. Texting is a great tool to help you relax your nerves and get to know someone you just met.

You don’t need to figure out what to say on a whim, and slowly process the small talk until you reach deeper topics.

On the other hand, in-person conversations are better because you see his facial expressions and jump from topic to topic as they come naturally.

So, it really depends on the situation you’re in. But, regardless of how you’re talking to this guy, whether it’s on the phone, face-to-face, or text message, you want to keep the conversation flowing naturally.

If there’s a natural click, you won’t need much help. But these tips will help give you the extra support you need. It’s time to get chatting! [Read: How to keep a text conversation going when you have nothing to say]

1. First, take a breath

This guy, no matter how dreamy or perfect he might seem, is still just a guy. He’s just as human as you are, and he’s not above you. This means you shouldn’t really be putting him on a pedestal.

So the best thing you can do in knowing how to keep a conversation going with a guy is just to breathe and calm down. The more anxious and nervous you are while talking to him, the more likely you’ll make a fuss out of things.

That’s not the first impression you want to give now, is it? [Read: How to stop feeling awkward around your crush and get their full attention]

2. Do you like this guy?

This is the question you need to ask yourself instead of just wondering how to keep a conversation going with a guy. Do you actually like this guy? Or is there another reason why you’re talking to him?

You should figure out before anything else if you really like him, not just because you’re lonely or bored. Those aren’t good reasons to start a conversation with a guy.

If you like him, then go for it. If not, save yourself some time and move on. It’s harsh but true. [Read: How to know if you like a guy – 15 feelings you can’t fake]

3. Stay true to yourself

Sometimes, we’ll change the way we behave to impress a guy we like. But the thing is, it never works. Stay true to yourself and be who you are.

This is the one piece of advice that’s probably said too much on how to keep a conversation going with a guy, but is vital to the core. You want him to like you for you, not for the person you’re pretending to be.

It can be so exhausting to pretend to be someone else, so why bother? No matter how dreamy he might seem, he’s not worth putting up a front for. [Read: How to be true to yourself and live life on your own terms]

4. You cannot be the only one talking

It’s tough to have to carry out the conversation for the both of you. If he’s dry at texting, there’s no need for you to carry him just for the sake of having a conversation – it’s just not worth it. He needs to be engaging and investing the same amount of time and energy. If not, you’re giving all of yourself to someone who doesn’t fully care.

It’s better to find someone genuinely interested rather than talking to someone who makes it feel like you’re talking to a rock! [Read: Is he shy or just not interested? 15 signs to decode his behavior]

5. The conversation should end

Yes, at some point, the conversation will need to end. This doesn’t mean you won’t talk anymore. But, it’s better to end the conversation, rather than have it linger on and on with one-worded replies.

You can try again in a few days, but it doesn’t mean you have to end the conversation in such a dry and stiff way. Make sure you end it on a good note!

6. Show off your personality

This is your time to shine when you’re trying to figure out how to keep a conversation going with a guy. If you’re in a face-to-face conversation, great, it’ll be easier to show him who you are. This is your chance to show off your personal sense of humor and the beauty of your personality!

What keeps a guy hooked in conversing with you is how admirable your personality is, so don’t hide it. Crack jokes, use memes and GIFs to your advantage! [Read: 18 texting secrets to go from timid to text temptress]

7. Ask him questions

If you want to get to know him and keep the conversation going, then you need to have things to talk about. Sure, general topics are fine, but eventually, you’ll need to dig a little deeper. Guys aren’t interested in superficial questions or small talk because guaranteed, they’ll be bored in minutes!

They don’t care about the latest gossip or how the weather is today. Ask him open-ended questions that don’t end in ‘yes’ or ‘no’ answers to keep the conversation going. Also, make sure he also asks you questions, so there’s a mutual exchange of conversation.

If he doesn’t ask you questions, you have to ask yourself if he actually wants to get to know you. [Read: Subtle and flirty questions to ask your crush]

8. Don’t overanalyze the conversation

We know how much you probably like him, we really do. But you can’t keep overanalyzing everything he says, or you’d end up losing your mind entirely! Go with the flow and your gut instinct in your reply. Overanalyzing will only drive you nuts.

Overthinking will only end up potentially damaging your connection with this guy since you’re stressing yourself out over nothing. We know how easy misinterpretation is on text messages, but your worst fears aren’t usually what they mean! [Read: How to stop overthinking: Secrets to go from overthinker to relaxer]

9. If you’re texting, don’t write an essay

If you’re going to write paragraphs and paragraphs of texts, you should know he’s probably not going to read them. Or maybe he will, but you won’t get an equally long reply.

There’s no need to impress them by writing a long-ass text! Keep your texts short and concise, and leave the long texts for when you actually get together.

It puts the element of mystery at play without making them bored with texting you. [Read: Here’s what to do when a guy doesn’t text back]

10. Share personal stories

If you want to take the conversation to the next level, you must create trust between one another. The only way to do that is to build a bond. Sharing personal stories is how to keep a conversation going with a guy without them getting bored altogether.

Share personal stories that you think would be interesting for him to hear, and he’ll take this as an assurance that he can also share stories of his own. Trust us, these text conversations make talking to one another more fun! By opening yourself up, you’re letting him know you trust him.

11. You don’t need to keep the conversation on text

Of course, in the beginning, you can text him, but after a while, why not send a voice message? Or better yet, why don’t you talk on the phone or via FaceTime? Texting is fine, but after a while, it does get a little boring.

Text messages are nothing compared to video calls with the guy you like. In fact, as convenient as text messages are, nothing gets more personal than face-to-face conversations *no matter how awkward it can get!* [Read: Why do men hate talking on the phone?]

12. Move the conversation to a real-life encounter

Do you really want to stay texting him for the rest of your life? Of course, you don’t. Your texts should eventually achieve a goal. Is your goal to land a date with him?

It’s perfectly okay to initiate a coffee hangout, especially when you think he’s shy about asking you out. After this, let him make the first move. Sometimes, all a guy needs is a nudge to take things further. Take the power and put it in your hands. [Read: 15 moves to ask a guy out over text and get the answer you want]

13. Is he interesting to talk to?

If you’re enjoying the conversation and you see that he is as well, the conversation will flow naturally. But if it feels like you need to pull answers out of him every time you ask him a question, that’s a sign the conversation needs to end. No matter how much you like him, there’s no need to force a conversation.

The more you force it, the drier it’s going to get. Sometimes, there just isn’t texting chemistry – and that’s perfectly okay. [Read: How to tell if there’s serious chemistry between two people]

14. Don’t second-guess what you want to say

If you want to say something, then say it. Don’t spend hours trying to figure out whether you should say what’s on your mind or not. He will take it however he’s going to take it.

We know you want to appear your best, but you also want to stay true to yourself. Stop overanalyzing things and just say whatever is on your mind *as long as it isn’t offensive, of course!* [Read: How to listen to your gut and give strength to your inner voice]

15. Just relax!

Seriously, relax. The conversation will continue to flow if there’s a natural connection between you. You also need to realize if it’s not a match, that’s okay.

You can let this person go and meet someone who’s more compatible. This is one of the most brutal truths to accept, but it can happen. After all, looks are nothing if there’s clearly a lack of chemistry and compatibility. [Read: What it means to date someone in reality – not the fairy tale]

16. Use humor

Text messages don’t always have to be so formal and stiff, you know? Using humor is one of the best ways on how to keep a conversation going with a guy.

It’ll catch his attention, make him laugh, and keep him interested in the conversation simultaneously. It also allows him to see who you really are without much focus on formality. [Read: How to be a fun texter & make them laugh while reading your texts]

17. Find something in common

You know how you could keep going on and on for hours about how much you probably love a particular singer or your favorite Netflix show to your best friend? The same concept applies to keeping a guy hooked in a conversation.

Finding common ground will have you talking about it for hours and exchanging opinions and ideas. This kind of common ground is also how you can test your compatibility and chemistry before going on an actual date.

18. Keep it light and casual

You don’t want to kill the mood of the conversation by talking about depressing and sad topics, do you? If you want to know how to keep a conversation going with a guy, then it’s all about keeping a light and positive tone. Don’t try to kill the mood with heavy subjects.

Life is already serious enough, and there’s no need to dwell on it constantly. Especially when trying to impress a guy, light and casual is the way. [Read: The best virtual first date ideas to really get to know each other]

19. Avoid shortcuts at all costs

It can be lazy to text all the time, so you end up abbreviating certain words. However, this can be a turn-off for some guys. It’s basic texting etiquette to at least use the complete form of the word instead of relying on shortcuts. Stop with the wyd? acronyms and use the complete sentence instead!

20. Live an interesting life

We know you’re probably thinking – what does having an interesting life have to do with knowing how to keep a conversation going with a guy? But this can make or break your entire conversation.

If you’re someone who just watches Netflix all day, waiting for a response from him, that’s not exactly an attractive trait.

Guys love texting those who live an exciting life, even if it takes you longer to provide replies. It makes for a great conversation, after all! [Read: How to be more interesting and make everyone rant to know you]

It’s time to start chatting!

By following these tips, you can interest a guy just enough to stay in a conversation with you. Don’t forget to be yourself, as when he sees the beauty of who you truly are, he won’t help but want to talk to you each day!

[Read: How to get over dating anxiety]

Understanding how to keep a conversation going with a guy isn’t actually as hard as you may think. As much as these tips can help, remember not to force a conversation when there’s clearly a lack of chemistry and compatibility. 

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The editorial team of LovePanky comprises relationship experts and real-life experts that share their experiences and life lessons. If you want the best love ad...