How to get the ball rolling with a shy guy

“A man’s vanity is more fragile that you might think. It’s easy for us to mistake shyness for coldness, and silence for indifference.”

― Lisa Kleypas, Devil in Winter

He may be anywhere, the university library, the local coffee shop, sitting at the desk next to you or even your next door neighbour. You see him almost everyday. Every opportunity he gets he says something to you. Unfortunately, it never progresses past the “We just got in fresh muffins”. Yet, you know that he likes you, it is obvious to you and everyone else, yet try as you may to get him to progress to the next level, he always ends up retreating behind his book or whatever prop is available nearby. You my dear, got yourself a SHYMAN.

It is easy to walk away and give up when faced with a Shyman, but if you do, you could be giving up on Abraham Lincoln, Steven Spielberg, Johnny Carson or even Mark Zuckerberg who was described Facebook COO Sheryl Sandberg as , “shy and introverted and he often does not seem very warm to people who don’t know him, but he is warm. He may be quiet, but he really cares about the people who work here.”

There are great advantages to having a Shyman, if only you can get him to open up and ask you out; even if it is only for coffee.

For starters, your Shyman will care about your feelings and will deeply listen to you. He understands and values emotion without being a doormat and chances are you will only need to tell him once your favourite book, place or how you take your coffee and he will always remember.

He will probably be one of the few men you’ll meet who will not keep remind you how f***ing great he is. He loves praise, don’t we all, but he is not a bragger!

He will put you first, listen to your problems and give you fabulous advice and he’s just so charming! Shyman will express himself through actions so expect breakfast in bed, flowers and random love notes. He’s never NOT adorable. You are a lucky girl.

So how do you get Shyman to talk to you? Try to find out what makes him comfortable and stir the conversation to that topic. For instance, he may be shy in school but not so shy when he is talking about his favourite hobby. Most times shy guys tend to be more lively in certain environments than others. Use this to your advantage.

Shyman may risk smiling at you. He normally does not do that because he is too embarrassed. Pay close attention to his smiles. You may have a guy who is incredibly interested in you. If he goes one step further and offers to help you then you are on to a sure thing. Did he offer to reach that high shelf or held open the door for you? These are all good signs.

You may be getting mixed signals from your Shyman. It is maddening, but don’t get discouraged. One day he musters up the courage to ask you about your favourite book and the next day he is looking at his shoes as you walk by all decked out in your specially picked outfit. All it means is that he is terribly nervous, and he does not know what to say. Cute, eh?

Pay close attention to his friends. If they are unusually sarcastic and tease him mercilessly when you are around, they know something you don’t. He has a crush on you!!! Shyman hates socialising, if you find him to be unusually chatty and accepting invitations to social events he would normally avoid, it is a clue. If he is willing to go through the pain of being around strangers and making small talk, he is really falling for you.

So, we determined that he is a good catch and that he likes you BUT, and this is a big but, he never asks you out. You and Shyman have become really good friends but things seem to have stopped there. He is probably too afraid of rejection to take it to the next level and he is hoping you will make the first move. In the case of blushing Shyman, this is exactly what you should do. Here are some strategies that will get your relationship out of the friendzone.

When you see him, smile, make eye contact and hold it a couple of seconds longer that you would with a friend. Try to make physical contact whether it is by pushing back a stray hair, fixing his collar or taking a pen out of his hand. Touching appeals to a primal instinct that he will not misinterpret. If appropriate, tease him gently and squeeze in a wink if you can. This is undercover flirting at its finest. Flirting that is daring enough for him to become confident but not so daring where he feels like he was ambushed. No guy likes that no matter how shy. If he does not respond immediately, give him a few days and try again ideally after you put a couple of drinks in him. If this fails as well then you misjudged the signs and Shyman is not shy, unfortunately he is just not into you.

“Like shyness, cowardice cannot swim in alcohol.”

― Mokokoma Mokhonoana

Author of the Dream series for women, I love to help women find happiness.

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