Help me overcome my shyness to talk to him?

[Cali]

I recently added this guy on MSN, after I finally got a mutual friend to tell him that I have a slight crush on him. We talked for a bit, exchanged hellos, how are yous, that sort of thing, then I found myself not being able to finish the conversation because I'm terribly shy/nervous/timid. Is there anything I could say to him to start up a good conversation or something? I understand that being myself is a big thing, but it's hard when I'm a little shy at first.

[Midnight Madness]

The question is: how much do you know about him? If you know what he likes, and are into any of it, start talking about how you feel about those things, and don't be worried about disagreeing. If you don't know, just ask him the things he's really into, then start talking to him about anything you know - be it asking to acquire more knowledge, or just opinions and/or feelings. Talk about funny things that happened during your day, and be open to listening to things he has to say - including about things that are worrying/bothering him, if any. But let those come out on their own.

Try to talk about things that are gender neutral or something he'd probably be more exposed to, but you can also fill him in on details of things that only you or your friends get (or try to, haha) to make him feel a little included. But remember, don't get lost in your own thoughts on these things as to dominate the conversation - share the chat, and make him feel interesting and included, like the things he says matter to you.

Be friendly, be thoughtful, be interested, and most importantly, be yourself.

[Cali]

The question is: how much do you know about him? If you know what he likes, and are into any of it, start talking about how you feel about those things, and don't be worried about disagreeing. If you don't know, just ask him the things he's really into, then start talking to him about anything you know - be it asking to acquire more knowledge, or just opinions and/or feelings. Talk about funny things that happened during your day, and be open to listening to things he has to say - including about things that are worrying/bothering him, if any. But let those come out on their own.

Try to talk about things that are gender neutral or something he'd probably be more exposed to, but you can also fill him in on details of things that only you or your friends get (or try to, haha) to make him feel a little included. But remember, don't get lost in your own thoughts on these things as to dominate the conversation - share the chat, and make him feel interesting and included, like the things he says matter to you.

Be friendly, be thoughtful, be interested, and most importantly, be yourself.

I know he's really artistic! But wow this is great advice! How would I sort of put that into words though? By starting it off I mean xD!


But thank you so much for the advice

[Midnight Madness]

Really, it depends on how you personally approach conversations in general. I'd say just bring it up casually, like, "so, what are some of your favorite things?" You can replace the "favorite things" part with any subject matter you'd like to constrain it to, like colors, games, movies, or considering his interest in art, who his favorite artists are or his favorite art styles.

It might feel a little awkward at first, but once you get talking about it, trust me, that will go away. Those first words are always hard, I know. And it's really stressful when you try to think of something to say, and you get discouraged because you think of how someone else might take it. But don't worry! Lots of people will understand what you mean when you say it, so don't be overly scrutinizing with your words. It'll start moving along, don't fret~ Things will keep getting better the more you get to know him.

[Byracka]

By experience, conversations tends to tensen up if you think too much before you say. What would have been a completely fine thing to say gets turned and examined in your mind until you think it's the most idiotic thing ever and that the other person will hate you. If he's a genuinly good guy he wont mind if you say something awkward or wierd or odd.


I dislike the phrase "be yourself", we are all ourselves in one way or another. It seems better to say "be your best self" that awesome person you know you can be. So how do you find your best self? I'd suggest that you try to talk and hang out with people you think seem fun and interesting. Eventually you'll just learn from those people how to be relaxed and flowing.


And as Sytex said. It will become easier as you get to know him 

[Cali]

Thanks for all of your help everyone!


I started asking him more questions and stuff, but I'm getting the impression he's not all that interested in talking? I dunno, might just be me feeling insecure, but I feel like I've run out of stuff to ask now v___v, I asked about family, valentine's day, travels, etc etc but I feel like this conversation is a one way street and I'm the only one on the street

[NovaAurora]

I know that whenever I find myself starting to run out of questions, what often helps is to try and center the conversation around a topic that doesn't require you asking anything. Once he's answered your questions, there's not much else that he can say and not have it sound like a non sequitur, so he might just not say anything at all. Then of course you have to ask again, which means he gives you the answer, and then there's nothing else to say again etc etc. Ideally he will ask questions back about you, but that could really depend on the subject matter. If you can somehow bring up a topic that is self-sustainable, that is you two have a mutual interest in it so you can keep the conversation going just by making random comments about it, I'm sure you'll find that conversing is a lot easier and less strained.

[Cali]

I know that whenever I find myself starting to run out of questions, what often helps is to try and center the conversation around a topic that doesn't require you asking anything. Once he's answered your questions, there's not much else that he can say and not have it sound like a non sequitur, so he might just not say anything at all. Then of course you have to ask again, which means he gives you the answer, and then there's nothing else to say again etc etc. Ideally he will ask questions back about you, but that could really depend on the subject matter. If you can somehow bring up a topic that is self-sustainable, that is you two have a mutual interest in it so you can keep the conversation going just by making random comments about it, I'm sure you'll find that conversing is a lot easier and less strained.

Well he hasn't really asked me questions himself even though most of the topics I've asked he mentions he really likes and stuff, but I'm having a hard time right now, but I guess it's because I've barely gotten to speak to him before