16 Effective Ways To Keep A Conversation Going With A Guy

The key to keep a conversation going with a guy (or girl too, actually) is to keep it interesting. Here’s showing you 16 ways how!

16 Effective Ways To Keep A Conversation Going With A Guy


  1. Keep the conversation interesting to keep it going
  2. #1 Be genuinely interested to know the guy
  3. #2 Get learning about his favorite topics
  4. #3 Ask questions about his childhood
  5. #4 Ask about his job and workplace
  6. #5 Talk about a picture he posted on social media
  7. #6 Make sure you have knowledge on various subjects too
  8. #7 Keep the conversation warm, friendly and funny
  9. #8 Avoid sensitive questions like past relationships
  10. #9 Ask questions that makes the guy think
  11. #10 Share your own experiences
  12. #11 The right body language can help the conversation
  13. #12 Avoid being too available to the guy
  14. #13 But keep inquiring after him regularly
  15. #14 Avoid complaining, judging, bitching
  16. #15 Give the guy some space
  17. #16 Have a life of your own
  18. Hit the guy up for a conversation he won’t forget!

Keep the conversation interesting to keep it going

Ask yourself, would you want to keep talking to a guy if he made you yawn like 15 times in 7 seconds? Of course not! But you’d certainly lose track of time if you were in conversation with a guy who made you laugh all the while. The same goes with guys. Yeah, they’re not from Mars as popular opinion has it. The same rules that apply to you, apply to them as well. If you’re interested in a guy and can’t get enough of him and wish the conversations with him never end, you gotta keep things interesting. And that doesn’t involve nudes (although that’s a matter of personal choice). But this discussion is about more non-PG level techniques to keep a conversation going forever, both over text or in person. Let’s get to them:

#1 Be genuinely interested to know the guy

najxoo's post
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I know you’re like, Why would I even bother if I wasn’t interested in him? But often, we like a guy because he’s cute or hot, but do we really want to know about his passion for being a Dungeon Master (this is just a video game, not THAT kind of role playing, silly)? You have to be really, genuinely interested in knowing all aspects of him for a conversation to be mutually interesting and therefore, steady. If you’re not, sooner or later you’ll find yourself bored and sooner or later he’ll find that out and lose interest and motivation to keep talking to you. Ask questions and learn about the guy with real enthusiasm and excitement.

#2 Get learning about his favorite topics

jaime.richter's post
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It is all right to take inspiration from a '10 best conversation starters' article, but it is unsafe to assume that you know what his interests are. Just because someone said that guys are sports freaks, it might not be exclusively true of your guy. He might hate the obsession over sports for all you know and talking endlessly about Manchester United vs Chelsea will lead to nowhere. So before you jump to start a carefully planned conversation, learn about his favorite topics first. You could ask him about his hobbies, for example. If he watches a lot of movies, it’s a great place to start the conversation. He might also be passionate about politics and social work, which make for good conversations too.

#3 Ask questions about his childhood

allthatisshe's post
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Even if the guy has absolutely no hobbies, interests or passion (that isn’t usual TBH but for the sake of discussion, let’s say he’s an alien in disguise or something), there are a couple of things anyone will always have a lot of talk about. His childhood, for example. Ask him where he grew up, about his family and his childhood friends and whether he’s still in touch with all of them. There’s something about nostalgia that makes people keep talking. This is a great way to ensure a long conversation without even having to try too hard. And if he’s really an alien after all, maybe you’ll learn some cool things about a different planet too.

#4 Ask about his job and workplace

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Another common topic that can keep a conversation alive even if there’s not much else to talk about, is work. If the guy is an adult professional, he’s spending most of the time in a day working. Naturally, he has a lot of talk about on that front. The projects that he’s working on, his boss who gives him a hard time or a colleague who makes life easier at work for him — or something along those lines. If you show real interest, he might also gleefully delve into minute details of the current project he’s been passionately working on. You might also become his favorite go-to person whenever he needs a listening board for problems with work he can’t discuss with anyone else. Longterm conversation benefit!

#5 Talk about a picture he posted on social media

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This is a great way to keep the conversation flowing over text. You can use the excuse of commenting on the guy’s recent social media activity. Maybe he’s posted a status update you have an opinion to share about (even if you don’t, just get with it!) or he might have posted a picture, in which case, a compliment is a must. In order to make the conversation go even longer, ask him specifics about the picture instead of just a compliment. Like, who took the picture, where was it shot, it looks like a great place to have a beer in, etc. Taking note of his activities also makes him see that you’re interested in him, which is reason enough for a guy to want to make a conversation with you. However, take care not to make it look like you’re stalking him all day. That’s not fun, that’s crazy.

#6 Make sure you have knowledge on various subjects too

fattykatzecandles's post
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All said and done, a fun, naturally flowing conversation is much more than a handful of techniques and conversation starters. It is about real knowledge. If you don’t know stuff, you can’t talk about stuff. Some common topics that make for long, continuing conversations, either through text or face-to-face, are current trends, global issues, etc. Read the newspaper regularly, follow recent trends on Reddit, Huffington Post, or any of your favorite blogs. Don’t be the girl who looks great but is empty inside the head. Being knowledgeable isn’t just about impressing guys, it’s about actually knowing what goes around in the world, which is a very cool girl quality. Your knowledge on diverse topics will impress any person, guy or girl, and make a conversation with ANYONE last forever.

#7 Keep the conversation warm, friendly and funny

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Often, if there’s a romantic tension between you and the guy, there’s a lot of conscious hesitation to converse freely, because you want to present yourself as this perfect person, and avoid any awkwardness from being stupid. If both you feel this way, this could be one reason the conversation doesn’t last very long, even though you’re both interested in each other. You have to initiate the process of getting the comfort level on. Learn to let go and keep things down to earth, because that’s when it will put the guy at ease too, so he will be able to keep talking without the fear of being judged. Being silly occasionally is a great way to come closer to each other. Knowing that the other person is as human as us, helps us open up better. A warm, friendly conversation makes for a fun conversation, and who has ever passed on anything that is fun?

#8 Avoid sensitive questions like past relationships

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Even if you’re doing everything right, there are some no-go places that you need to be careful of. If you’ve been asking him questions about his life in general, you might get too close to asking him questions that the guy is sensitive to, and he might shut you off completely. It is okay to talk about love and relationships in general, but don’t get too personal with it unless he decides to bring it up himself. It is a great move to want to know about him — plus it is also natural to feel curious about who he dated and why they broke up — but know your limits and don’t cross them. If the guy feels comfortable enough, he’ll soon start pouring his heart out to you.

#9 Ask questions that makes the guy think

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Asking the same old tired questions makes the conversation dull in no time. If the guy has been doing this for a while, chances are high that he’s been answering the ‘What’s your favorite movie?’ or ‘What’s your favorite color?’ questions too many times for him to be even interested anymore. Steer clear of things that make him feel like he’s caught in a rut. Ask him thoughtful questions instead. Thoughtful here means, questions that makes him think hard before he can answer, and questions that makes him see that you’re a deep thinker too, not some shallow bimbo. And no, I’m not referring to tough GK questions (although if that’s your thing, no harm in trying), but questions about his mind and his dreams. Questions like what steps would he take if he were the President of the United States, or what his interpretation of the movie Forrest Gump is. Questions like these get you dive deep into your mind which is a treasure trove of discoveries that keep your conversation on for a long, long time.

#10 Share your own experiences

_karenlsc's post
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A follow-on from #7, a great way to make him feel comfortable to share his experiences at length is to share yours first. Pick the silliest, most awkward and funny incidents. Describe them at length. This will achieve two results. First, you’ll make him laugh which is a great attribute for any person to have, and he will remember conversations with you to be thoroughly enjoyable. Second, you’re basically showing him what he should do by ding it first yourself. When you open up to the guy without inhibitions, he will feel encouraged to do the same. And rest assured, most guys WANT to keep going about themselves, showing themselves off to you. All they need is a little assurance that you’re totally fine with them doing that.

#11 The right body language can help the conversation

terakeet's post
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Your interest in the guy, which is an important selling point for him to keep talking to you, can be expressed not just with your words but also with your body language. The guy might be reading his self-help articles too you know, in which case he knows that a girl who’s interested in him will show in the way she behaves. Make steady eye contact during the conversation, but not so much as to scare him off and make him stammer. Relax your posture and smile and laugh often, to make him feel like his efforts at making a conversation are working. If you’re chatting over text though, this won’t be possible. But over text, you can make up for it by using lots of relevant emojis or sending voice notes occasionally. Even if the guy is making the conversation, it is important that over text you keep sending your replies often because obviously he can’t see you listening to him.

#12 Avoid being too available to the guy

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This might seem like the opposite of what you should be doing, but it is important to keep things interesting because you’re creating an air of mystery about you that makes YOU interesting. And a conversation with an interesting person is undoubtedly interesting too. Don’t be an open book to the guy. If he learns all about you within a very short span of time, why would he bother to make efforts to keep the conversation going? He needs to feel curious about you and eager to know more with each passing day. Unfolding yourself gradually over a considerable span of time will keep him guessing and wanting for more. And when he does get to talk to you, he wouldn’t want to let go soon. Being too available, by that logic, likely does the opposite.

#13 But keep inquiring after him regularly

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However, your lack of availability shouldn’t be interpreted as a sign of arrogance or lack of interest. Make sure the guy knows that you’re not available for a conversation 24/7 because you have other things to do in life, not because you don’t care about him. To that effect, keep asking him about his day and his work or his family (whatever you talk about mostly) and ask him to fill you in on his life occasionally. He will appreciate your concern and see you as this person who stays busy but is still polite enough. More importantly, he will feel that you consider him important enough to find time to know about him, which will in turn make him want you more. This mutual feeling of care will keep the conversation happening for a very long period of time.

#14 Avoid complaining, judging, bitching

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From personal experience, most guys tend to be averse to negative conversations. Even in general, negative conversations are never a good approach to keep a relationship going for long. Be sure to stay away from any tendency to express negative opinion on someone you both know, a common friend or colleague for example, or to constantly complain about your situation or any other event. Also check any tendency to get judgmental about something you don’t like or don’t quite understand. Be accepting and accommodating of differences in opinions. You don’t have to be a Yes Man either; even if you both disagree over something, make it a healthy, constructive discussion. Complaining, bitching or nagging makes for a very tasteless conversation and even if you’re a great person otherwise, the guy will not want to keep taking more of it. Positives vibes that people feel when interacting with others make them come back for more.

#15 Give the guy some space

mallory.blayne's post
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If you’re really interested in this guy, you’d probably be wanting to talk all day all night with him (“Duh, Panda Gossips, isn’t that the reason I’m reading this article?”) But you can’t. And you certainly can’t try to force it on him. If his want for a long conversation coincides with yours, it will happen. But if he didn’t reply to your last text in 5 seconds like he usually does, don’t fret! The guy has his own life too. It is important to give him the space to do his own things and trying to suddenly demand a change in his routine will suffocate him and the conversation will be over for good. In fact, even if he doesn’t ask for space, be smart enough to voluntarily give it to him. For example, if you catch him on call or text when he’s watching a match between his favorite teams, be quick to say you’ll catch him after the match is over; don’t wait for him to ask for a time out. You’ll top his cool girl list instantly!

#16 Have a life of your own

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No matter how interested you are in this guy, don’t make your life and time all about him. Don’t text or call him all day and wait by the phone for his replies for the rest of the day. Not only is it unhealthy in a ‘putting all your eggs in one basket’ kind of a way (because, what will you do if for some reason he stops talking to you?), but also, if you have nothing going on in your personal life, you’ll soon run out of interesting topics to talk about. The conversation has to be a mutual sharing of things, it can’t just be about his side of the story. To keep it going for a long period, you need to take occasional breaks to do your own things while you give him the space to do his own. And when you get back together to talk after, say, a trip you returned from, or a killer work conference you slayed, you’ll create a more organically interesting conversation that neither of you will want to end anytime soon.

Hit the guy up for a conversation he won’t forget!

ivan_kaba's post
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These 16 steps should be more than enough to keep your conversation with this guy flowing endlessly, but like I always say, you’re going to learn so much more from actually engaging with him. Keep asking the right questions and keep up a positive attitude, and the guy will let you in on the secrets of a long conversation himself!



Monalisa Murmu
Lover of all things vintage.