I like it when it goes both ways.

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I'd strongly suggest reading JM Kearn's classic "Why Mr Right Can't Find You". It was written in about 2008, and stresses the importance of females approaching quiet or shy males. This helps greatly in avoiding the flashy "Alpha" types who can often take females for granted, and who are (biologically programmed) to initiate brief casual relationships with females.<br />
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I think this will explain a great deal.

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If I may.... Those you see and think you wouldn't mind asking out..... Are you forming a decision on their appearance because if you are you're going about it he wrong way. We all want to fall in love, I understand that but if you are going to great lengths too remain a virgin then walk the extra mile and fall in love with their heart. You can't do that unless you hear them speak and quite shy guys don't talk very much believe me I know I've struggled for years with it and even missed meeting some nice women because of it.<br />
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Well, I'm not going to leave you hanging there. What do I recommend ? believe it or not " do some research " on " Active Listening " it teaches you on how to engage into a conversation and how to keep that person talking.<br />
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Kinda see where I'm going with that ? There is a saying that goes: For what comes out the mouth flows from the heart.

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the problem in my specific situation is not with a shy guy, just one who's not the most skilled at picking up on "signals" or "hints" or even flirting. I'm definitely not in love with his looks - I mean, he's cute but that's not what drew me to him. I like him because I HAVE spent time with him, and gotten to know him, and he is a genuinely amazing person. He has no problem talking either, our conversations are very smooth and easy.
All I really wanted to know is what people thought about women making the first move (ie "asking a guy out") because I figure in my situation, if I don't I'm just going to end up more and more annoyed and frustrated!

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when I found out this guy liked me.. I went up to him.. and asked him about it.. lol. and he did.. and we became friends.. and then one day.. I was in love with him. and we dated.. no real official.. he asked me or she asked him or whatever.. it just.. happened. but I prefer a man.. show his interest to me.. If I liked him. I would tell him.. but I would never initiate a relationship. It's his job to win my heart. not my job to win his.. that's just backwards to me.

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I never liked doing that. I don't have the confidence it requires.

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