wikiHow to Keep a Conversation Going with a Guy

Three Parts:Knowing What to SayKnowing How to Say ItKeeping a Conversation Going Online or via Text

You might be passing time at a party with a guy you've just met or talking to the guy of your dreams on a first date, but if the conversation reaches a slow point, you might be panic-stricken about what to say to keep it pressing forward. Take a deep breath, calm down, and follow these helpful hints about how to keep a conversation with a guy going.

Part 1
Knowing What to Say

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    Ask open-ended questions. This technique is essential regardless of who you're talking to and what your end purpose is. An open-ended question will demand a more elaborate answer, while a yes or no question can be answered with a single word. If you want to keep a conversation going, open ended questions are more effective than questions that can be answered using one word.[1]
    • Find ways to rephrase yes/no questions into open-ended questions. For example, instead of asking the guy if he enjoyed the movie you watched together, ask him what he thought of the cinematography or the story.
    • You can coax his answer out by mentioning your own thoughts on the topic, but make sure you're leaving room for him to talk.
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    Create more questions based on his answers. In other words, use the information he provides to extend the conversation. If you're attentive, you can usually find something that he may elaborate on in greater detail. You can either use this method to extend the conversation in the same direction, or to change the subject to a new, related direction.[2]
    • If you can't think of more specific questions, you can say, “That sounds interesting. Tell me more.”
    • Don't interrupt him while he's talking. Wait until he finishes a thought, then ask additional questions.
    • A guy might stop talking about a topic if he thinks it would bore you. The beauty of asking him to elaborate on what he brings up is that it keeps the conversation going while boosting his confidence about his ability to keep you interested.
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    Offer a compliment to loosen him up. Most people appreciate a compliment when it seems genuine, and if the guy in front of you looks like he might be tongue-tied in front of you, he could probably benefit from the boost in confidence a bit of truthful flattery can provide.[3]
    • Avoid overly seductive or suggestive compliments. For instance, telling a guy “You have great eyes” is preferred over telling him “You have bedroom eyes.”
    • The best compliments will make him feel better about the circumstances as a whole. For example, try something like, “I'm really glad you've been keeping me company here. I think I would be bored out of my mind by now if not for you.”
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    Talk about the location. If you need a topic to bring up and you need it fast, take a look around. You can probably find something about the place you're in or the event you're at to talk about.[4]
    • If you're at a party or a social event, talk about the music, the decorations, the food, or anything related to the event itself.
    • If you're at a restaurant, talk about the ambiance, the food, and whether or not you have eaten there before.
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    Be positive. Complaints can misfire, and most people will be more interested in continuing a conversation with a positive, upbeat person. If you work together or go to school together, there may be plenty of incentive to whine. However, resist the urge to complain at length.[5]
    • Some ranting can create an atmosphere of camaraderie between the two of you, since everyone has work or school stresses, but if you complain non-stop without letting him into the conversation, he'll have no reason to stay in the conversation.
    • Instead of complaining, point out things that are going well. Talk about how your company recovered after a bad event, or how the new teacher is working out so much better than the old one did.
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    Ask him about hobbies and interests. Most people love to talk about things they're interested in. Once you know what he's passionate about, you can continue asking questions about it and building a conversation.
    • If it is a guy you do not know very well, you might have to dig around a little bit first to find out what some of his interests are. If you don't know him well, it's okay to ask him.
    • Try to find the things you have in common. You'll have a better time keeping the conversation going if you're able to talk about shared interests.
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    Tell a humorous story. People like stories, especially those laced with humor. If you can tell a story that only happened a few minutes ago, you should have little problem breaking the ice with the guy in front of you.[6]
    • An older story could also work out, but you will need to find a way to introduce it into the conversation. If something about your current circumstances tie into the story, you can say point that circumstance out and introduce your story with, “That reminds me about this one time when..."
    • Be aware that sometimes humor is risky. Not all cultures share the same ideas of humor, and you might think of a funny story that seems like a terrible social gaffe to him. Wait until you've got a sense of what he might find funny before sharing your own hilarious escapade.
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    Open up about yourself. Talking about yourself lets the guy know that you feel comfortable trusting him. That will inspire him to put a little trust in you. As mutual trust grows, the walls blocking conversation will start tumbling down.[7]
    • It's not a good idea to get overly personal right away. A conversation about when you got your first period might be a little too personal when you're getting to know a guy.
    • Talking about yourself in ways that aren't totally flattering makes you appear approachable to other people. If you only talk about yourself in glowing terms, he might feel intimidated.
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    Avoid talking about past relationships or dates. No guy wants to think about your history with other guys. Unless he's specifically asking you for information, your past is better left unspoken.[8]
    • Even if you're talking negatively about past relationships, he might get the impression that you're still hung up on your past beau.
    • If you just ended a relationship, the guy you're talking to might assume that you're "on the rebound."
    • If your ex was a friend, there might be a certain loyalty to his friend that will keep the new guy from wanting to continue the conversation with you.

Part 2
Knowing How to Say It

  1. Image titled Keep a Conversation Going with a Guy Step 10
    Look comfortable. Your body language can communicate that you're interested in talking with him - or that you'd rather leave. Keep your body turned in his direction, and your arms uncrossed. Leaning slightly forward towards him will also let him know that you're interested in what he has to say.[9]
    • Avoid fidgeting. If you feel the need to fidget, shift your physical position once and commit to it. Instead of freaking out about not having something more to add to the conversation, shift your thoughts to a new topic.
    • Do not worry about fidgeting or feeling uncomfortable. If you start thinking about it, you're likely to end up fidgeting more.
    • If you seem rigid or uncomfortable, the guy might think that you feel that way because of something he is doing wrong. This anxiety will only cause him to struggle further with a conversation.
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    Break eye contact from time to time. Even if the guy in front of you is real eye candy, staring him down will make him feel hunted. Keep your eye gaze directed towards him, but periodically glance away for a couple of seconds. Eye contact is important, but knowing when and how to break it is important, too.[10]
    • Eye contact lets a guy know that he has your undivided attention. If you're scanning the room, he might get the idea that you're looking for a better opportunity.
    • Rather than staring right into his eyes while you talk, catch his eye with your gaze, then look away, then back again.
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    Be expressive. Nod while he's talking to let him know you agree with him, or that you can relate to what he's saying. Smiling is especially important because it can help him think you're enjoying what he has to say. This will give him confidence to continue talking. Smiling also makes you appear more approachable, and less intimidating.[11]
    • Do not be afraid to express emotion with your hands, too. Many people talk while gesturing with their hands. If this is normal behavior to you, then don't worry about trying to tone it down or stop it.
    • Make sure your facial expression reflects the tone of the conversation. If the conversation becomes serious, grinning happily will make you seem detached from the conversation at best and sadistic at worst.
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    Show interest and attention. Do not split your attention between the guy you're talking to and something else—like a text conversation with a friend, for instance. In order to get the guy to continue talking, you need to let him know that you're listening to everything he says.
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    Do not judge yourself. If you accidentally say something foolish or embarrassing, acknowledge the error and move on. Everyone says something awkward every now and then. If and when it happens, just laugh it off as best as possible. Guys are quick to appreciate a girl's sense of humor.[12]
    • If anything, seeing you mess up and laugh it off will relieve the guy's tension and let him know it's okay if the same happens to him.
    • You can apologize for your slip-up if you feel the need to do so, but after apologizing, let it go.
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    Avoid seeming too eager. You might want to meet him again, but don't assume the feeling is mutual and begin planning your next date. As the conversation goes on, drop hints about how you would like to spend more time with him. If you drop enough, most guys will catch on before the talk ends completely and act accordingly.[13]
    • The best hint you can drop is simply saying, “I really enjoyed talking with you. I hope we can do this again sometime soon.”
    • If he doesn't ask you to get together again, give him your contact information. After all, he might change his mind.
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    Know what his silence might mean. Silence is not always as bad as you might think. It's possible that he isn't interested, but it is also possible that his nerves are just getting the better of him. Cut him slack and try not to persecute him too severely for his silence.[14]
    • If a guy is intentionally making his answers short and he seems distracted, he probably is not interested. That doesn't mean there's anything wrong with you. He probably has other things happening in his life.
    • If a guy seems cold and brief as he talks but his body language suggests that he wants to stick around you, he might just be using his coldness as a way to cover his own feelings of awkwardness.
    • If the guy seems intimidated by you, take things slower and lay off on the flirting.
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    Eliminate or reduce romantic tension. If this is a guy you're interested in romantically, this piece of advice might seem counter-intuitive. By fixating on creating a romantic ambiance, though, you might make it harder on the guy to relax long enough to converse with you.[15]
    • Reduce romantic tension by cutting back on any verbal or non-verbal flirting you might be doing.
    • Keep your words and actions restricted to those you might use for a male friend or male relative.

Part 3
Keeping a Conversation Going Online or via Text

  1. Image titled Keep a Conversation Going with a Guy Step 18
    Mention something you saw on his online profile. If you are talking to a guy via the computer, check out any online profiles he has given you access to and bring up information he has posted publicly. Compliment him on something he's posted, or ask him questions about someplace he's visited.[16]
    • This works especially well if you are talking to someone via the messaging system of an online dating website, but it can also work if you are messaging something using a social media outlet.
    • In addition to posting about things the guy said, you can also ask him about photos on his page. For instance, if his profile picture shows him standing in a forest, you can ask him where he was at in the picture and remark on how lovely the surroundings are.
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    Keep it casual. Friendly, entertaining texts or online messages can be a fun way to continue a conversation. Deeper conversations need to happen in person. Don't ask him too many personal questions through text or online, unless he's made it clear that he's comfortable talking this way.[17]
    • Being funny, and adding emoticons, helps keep a conversation going. Even a single smiley face or wink can help shape the tone of your text in a light-hearted direction.
    • Texting can be a great way to give him little compliments.
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    Reply within a reasonable amount of time. When talking to a guy through email or social messaging, reply to him within the same day, if possible. If talking to a guy via text message, try to respond within a few hours.[18]
    • You do not need to reply right away. Replying to an online message within an hour or so is fine.
    • Make sure you're not always the one sending the first text. Give him a chance to miss you.
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    Keep messages short, but meaningful. If this is a guy you see in real life or hope to see in real life, then you should save most of your long conversations for meeting in person. That said, you should talk about things more significant than the weather when you talk via text or email.[19]
    • Ask about weekend plans and major projects going on at work.
    • Avoid asking for advice on significant dilemmas in your life or opinions on hot political issues.
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    Avoid over-texting. If a guy does not reply to your first text or online message, resist the urge to send him another an hour later. Give him some time. If a few days pass, you can try again. Texting or messaging more than 2 times without a response can appear creepy.[20]
    • Don't ask him why he did not reply to your first message, unless this happens repeatedly.
    • If you do decide to ask him why he didn't write back, ask in a polite way. Blame technology if all else fails, and say something along the lines of, “My phone has been having issues lately. Did you get my text from a couple of days ago?”
    • You could also gloss over the first message completely and move on to another topic of conversation without bringing up the fact that a message was ignored.
    • If a guy does not reply back to this second message, however, do not bother with a third. The conversation has effectively died at this point already.
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    Make up for the lack of body language. Conversing with a guy through digital means has one major disadvantage: there is no way for you to speak non-verbally. To make up for this, you need to use phrases that express feeling as well as information.[21]
    • For instance, if the guy compliments you, say something like, “Aww, gee, thanks!” to express gratitude and imply that you are bashfully happy about the compliment.
    • A sprinkle of emoticons can also help, but don't get carried away. Only use emoticons when you want to emphasize or clarify an emotion.


  • Keeping a conversation going is a 2-way street. Make sure to leave room in the conversation for him to keep up his side of the conversation.


  • Even if a conversation is going really well, don't make plans to meet someone you don't know in a private place. Keep yourself safe by meeting only in public areas until you know him better.

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Categories: Conversation Skills