Advice on keeping a conversation with a boy?

I saw that guy on Facebook and I texted him like "Hey, nice hat lol" (Okay, don't judge me, I know I suck at this) and he replied "Lol yeah but it's not mine lol" And then we exchanged the ordinary questions "What are you doing, where are you from and have you ever been in the city I live" (we live in different cities, far away). From now on I don't know how to keep the conversation going right.
So I need your advice on this, I don't want to bore him with questions like "yo what's your favorite color". I want it to be kinda interesting conversation, ideas?


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Most Helpful Guy

  • If you're stuck, ask the golden question or a variation of it. "Tell me more about that." This is brilliant because not only is it continuing the conversation and opening up tons of opportunities for more conversation but it shows that you're genuinely interested in what he's saying and you're also letting him take the conversation in whatever direction he wants. When he told you that the hat wasn't his, you should've asked him who's was it and then asked him about the story behind it. That would then open up lots of different conversation paths. You could pick out bits of the story and ask him about them in more detail, possibly opening up more stories. It's actually not that hard. So always look for more detail when he tells you something.
    Hope this helps :)

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Most Helpful Girl

  • When he said the hat is not his, you could habe said "whose is it? Maybe you should geht one cause it looks good on you".

    Just find something to ask or say based on what he said. And if anything random occurs in your mind, ask him. Ex: "Nicki minaj, hot or not?", "do you like the 90s/80s/00s fashion/music?"

    Just talk about anything! Share interesting stuff you find on the internet. Then you can discuss about it. Open up to him a bit.

    It is, however, a 2 man job. He also has to habe the personality for it. It he's the type of pea-sized boy who only gives yes or no answers, don't waste more of your time and just move on

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What Guys Said 24

  • The best way to talk to a guy over tech is to set up opportunities for him to be funny.

    For example when he said "it's not mine" you could have followed up with "did the owner put up a fight?"

    Though not funny on your end, it's open for a joke. This also allows you to gauge his intrest in you (ie, making a bloody effort) as well as see if he is clever.

    Good luck

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  • Something you may wish to keep in mind, boys your age (I mean no offense by this) often find it difficult to converse in the best of situations. This is true for a couple of reasons. 1. they are teenagers, and while not impossible all those hormones coursing through their teenage bodies don't really predispose their brains to make complete and coherent sentences. 2. Many young men aren't terribly well versed in making conversation anyway. Does it mean it's impossible? No, just rare, and regrettably most of your well versed teenaged boys are the ones who read, and attend classes regularly (nerds, not judging here, as I'm a nerd too) Lastly and most unfortunate American culture doesn't tend to encourage communication skills for our males, as many male role models are athletes (nothing wrong with this), or other "action" based sorts of figures. To be sure some of these ideas are changing, however change in this area is slow, so be patient. Can you find boys within your own age group who can converse? Yes you can, but know it is far more the exception than the rule.

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  • Conversation outside of face-to-face interactions are going to get boring quickly no matter what. Phone calls can be a little better because you can hear each other's voice, but face-to-face conversations are always going to be the best.

    I assume you're messaging him because you're interested in him? If so you should just ask him out, but if you live too far away then you're pretty much out of luck. I wouldn't recommend a long distance relationship, but if you do want to try it then stick to phone calls or Skype video chats. The closer you can get to face-to-face the better.

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  • You can always keep a conversation going -and it won't be boring - by asking the other person questions that get them to talk about themselves. Where did you grow up? Public or private schools? Do you like sports? What kind of music have you listened to in the past? What do you feel passionate about? What do you think you will be doing 5 years from now?

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  • honestly if a girl was wanting to get to know me, even by asking what my favorite color is, as long as she is participating in asking the questions and its not just me, I'd find that very flattering. the fact that someone wants to get to know me is always a good thing! most questions I don't find boring... now one to two word answers... oh god that kills it very quickly for me. I like the girl to be involved in her answers. NOW I will say some questions only warrant 1 to 2 word answers like whats your favorite color and thats fine, I'd know that going into asking those questions. start to ask tougher questions when you get done with what I call the basics "what is/ are your favorite...". asking them what their goals are in life and how they plan to achieve them. ask them questions that require longer answers, that way you have a better chance of being able to build a conversation off of them.

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  • Bring philosophical questions into the conversation. Where do you see yourself in X months/years. What's brings meaning to your life.. previous relationships, and discuss the reason why they didn't work out, (but not in a personal way, more in wide terms, the theme of relationships). Discuss politics, football.

    Don't ask those questions directly, bring the theme up by sharing your opinions, experiences beliefs. It usualy gives room for plenty of talk and freedom to change topics.(If you reach sexual relationships from the previous, it may get awkward or very interesting, it's a risk work taking)

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  • Just keep asking questions. Not like favorite book, or sport, but goofy ones, ones you would ask as a child.

    Ask if he plays an instrument, why he chose it, or why he doesn't, but don't be like a mom about it, keep it light. If he likes an article of clothing, that hat, ask why.

    My advice would be to give him opportunities to tell a story or be funny, not just answer a question, the easiest way to do this is just ask why.

    Ask where he wants to live when he retires, and then why that place. If he wants kids and a wife, or if he wants to be a bachelor, and then why. If you ask simple questions and then why you can find out more about him really quickly and it keeps your conversation going, and if it lulls tell a story about something you have, if you have a hat you like a lot, where you want to live.

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  • Okay. I haven't finished reading this. I am in the second line and omg u people say LOL a lot. Anyway , i keep on skipping girls that ask me these normal boring "wh" questions. I am talking about these convos :
    -Hi
    _hi
    -How r u?
    _Fine. u?
    -Fine
    _What are u doing?
    -Nothing. u?
    _Nothing.
    - k
    That is just terrible and unfortunately , this is how most of us , the teenagers talk. That is plain bad. Now thankfully , i am not one of these people. I know how to keep the convo interesting. And i never start the convo with "wh" questions. Just go to omegle. com and practice there ok? Talk to random non-horny guys and try to keep the convo alive. I can keep the convo interesting when i am talking to a stranger for at least an hour and a half.

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  • ok i want to message you an image that has 40 questions or things to talk about with a guy it's a really fun game and increases sexual tension and that is what you want if you like the guy.

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  • I'd recommend actually getting on voice with him.

    Seriously, 80% of people fucking suck at text communication. Just get them into voice and you can see just how good of a conversationalist they are (it'll also help you out too, providing you're not autistic and aren't good at talking in voice).

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  • "yo what's your favorite color" lol.

    Ask some open-ended questions. Although it's unusual coming from a girl, it'll show you're really interested in knowing more about him.

    quick example:
    - " If you could only choose one person to bring with you on a trip, who would it be and why?"

    try to make it relevant to you or him in some way.

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  • Wow this question made me feel so much better... because I always have this same problem... I guess it's just a universal problem...

    there is no "easy" way to keep a conversation going I suppose... and it really all boils down to pointless talk with no substance, doesn't it?

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  • Tell about somethig you have experienced at school or work lately and ask him if he ad the same experience... something like that

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  • There is lot of questions you can ask him ,
    Hows the weather where you live? Have you ever
    traveled out of the country? How long have you been
    using Social Media? etc.

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  • Hey if it flows it flows... if it doesn't it doesn't

    You should naturally want to engage in whatever your mind comes up with... and if it comes up with nothing then say nothing, if he's right for you... he will do the talking

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  • The main things is to ask him questions, and to talk details about what he said.

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  • easy, ask questions and never give one word answers (mkes you look disinterested)

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  • Be random. "Holy shit! Did you know Iggy Azalea has a fake accent?"

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  • What are your hobbies?

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  • HOT GUYS GONNA HOT.

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  • Ask him about religion and politics and he might as well be on drugs ;)

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  • I've always tried giving the conversation some fun when I'm talking to anybody, I don't really message anybody first (Which I'm working on) but for the people I do I keep it positive like "Hey! How's you? :)" Or to some of my best friends "Oi dickhead ;)" Etc, you can get the idea.

    Conversations do last longer if there's good energy, a constant "lol you okay?" "lol yeh u" sort of thing is just bland and irritating, plus lazy typing like that. I've usually liked sassy girls that push your buttons a little (Playfully of course) that just makes the conversation interesting, but there's a limit from being playful and annoying. many girls don't realise this. Men are simple we don't play mind games as much as women tend to do, if you act disinterested we'll just take it you're disinterested.

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  • I feel you. this is why I avoid online conversations with strangers. so often they reach a point where they stall out, you run out of things to talk about then just resort to asking questions to spur conversation.

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  • lol... social skills. I dunno how I end up talking for 6 hours straight to girls but I just do.

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What Girls Said 10

  • Send him links to interesting articles or funny YouTube videos

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  • Honestly if you click it kinda just happens and you don't have to put thought into it. If you don't click, then you find yourself asking strangers to basically carry on a conversation for you.

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  • Ask him questions about himself. Everybody likes to talk about themselvesXD

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  • I think it's a little easier when you Acthally kind of know the guy. If he was just someone from Facebook you added, it might be hard to start a convo. But if he's from school or you met and talked awhile on dating site or something, then you can at least talk about that.

    I personally wouldn't add a random guy from Facebook who I didn't know

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  • Ask him what he likes to do for fun I don't know like see what he's into music festivals, concerts, hobbies pets lol if you guys are comfortable enough with each other talk about relationships that always makes a long interesting conversation

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  • Find something mutual, like if he is in high school too ask him what he wants to do after graduate? Or ask his opinion about something popular or goes viral now, meme and some slang words.

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  • Just be yourself... most of the guys love it when we feel comfortable talking to them... you can always get to know his likes... how his day was? Stuff like that...

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  • Talk about hobbies, family, movies, sports or what you wanna do in the future :)

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  • where did you find that guy on facebook? just a random guy?

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  • Try playing the 20 questions game!

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