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How To Easily Approach A Shy Guy

Fresh perspective on dating issues compiled in consultation with friends in North America, Australia and African nations.

Guys are often the ones who make the first move when it comes to dating, but this may not be the case for men who are too shy to approach a girl. Shy guys (like all other men) have feelings and are equally attracted to potential partners. But they may not speak up if they fear rejection. They often fear what to say if their offer to go out is turned down. Of course every man has an element of concern about rejection, but genuinely shy men often don’t have the nerves or the courage necessary to approach and start a conversation with a girl, despite being interested in her.

If you are attracted to a shy guy and are tired of waiting for him to approach you, it is time to take the lead. Start by letting him know you are interested enough to want to spend time with him. Get to know more about him, and watch for signs if he is really interested in you or not.

The most important thing is to open up to him and help him gain confidence to engage in conversations with you. After you get to know each other better, you can talk about the feelings you may have for one another. But the first approach should be building rapport between you.

Many girls find it difficult to approach shy guys they like, but don't fall into that trap. If you are interested in him, reach out! Here's a few tips to get you started.

It is pretty easy to spot a shy man. Help him feel at ease with you.

It is pretty easy to spot a shy man. Help him feel at ease with you.

1. Start a Conversation

He could be your classmate, workmate, neighbor or any other shy guy you happen to meet somewhere but what should you do if you are interested in him and he isn’t opening up to you? Shy guys are less likely to start a conversation with a girl but that shouldn’t be an excuse not to approach them if you happen to like them.

If he is not ready to start a conversation with you due to shyness, procrastination or fear factor, it’s important that you be bold enough and approach him directly. What you can do to get his attention is to drag him into an issue and strike up a conversation with him. Here are some of the things you can drag him into that can necessitate a conversation between the two of you.

  • Ask him a question or something which obviously you know its answer. If he doesn’t know the answer to the question, you can answer the question and claim that you have remembered. By this time a conversation must have taken place between the two of you and even though the topic of relationship may not come up at this time, it could follow as you continue to get to know one another better.
  • Inquire about or kindly ask whether he can help you in doing some assignment. If he is kind enough he will most likely answer to your call and assist you in your assignment and by the time you are done and say thank you to him, you will have became familiar with one another which means starting a conversation with him the next time should be easy and after that is when you can pursue your goal of having a relationship with him.
  • Ask him about his favorite sport team or the kind of music he listens to. Men love sports and especially football and that could be an opportunity for you to approach and start a conversation with a shy guy. Do some research to figure out what his sporting passion is. His friends will probably give you a few clues. For instance you can ask a question like, 'Which team do you support in the English premier league?' Chances are he will respond and his answer could be 'Manchester United' or 'Arsenal'.

    Ask him as many questions as possible about the team he supports and you'll have paved the way for future discussions that can be used to bring up the topic of relationships, and the chance to let him know you are interested in him.
  • Ask for directions to somewhere. Anywhere. Just a quick and easy question that requires a quick and easy response.
  • Ask to borrow something. Anything. It might be a pen to jot a note about something you want to remember, or perhaps his phone if you need to make a quick call home and your phone's battery is flat. (That's a good way to make sure he has your number!)

Once you've had one conversation, no matter what it was about, the foundation is in place for future conversations. You just keep saying 'hi' and talking about whatever springs to mind every time you see him.

If your shy guy can see that you are approachable and willing to talk with him, he should become comfortable enough to approach you and talk. It generally takes time for a really shy guy to relax enough to openly communicate with a girl he likes, but it happens a lot. You the start the conversation and he'll do his best to continue it.

2. Chat With Him Online

Chatting online with him could also be a way of approaching a shy guy. Remember that the online world is anonymous and anybody can say whatever they want because no one is seeing them.

Online social networking sites like Facebook can become a platform for you to approach and have a conversation with a shy guy who is less likely to open up to you in the real world.

But remember, he's shy ... so don't paste your messages for everyone to see. He probably won't enjoy being teased or questioned about his relationship with you. Private messaging is his most comfortable option.

Let your shy guy hide behind his computer while you get to know each other.

Let your shy guy hide behind his computer while you get to know each other.

3. Listen To What He's Telling You

Shy guys rarely shout. They'll tell you things but you need to be listening. Sometimes it feels like they're dropping breadcrumbs instead of serving up an entire slice of bread, toasted and laden with toppings the way many guys (and maybe your ex-boyfriend) would.

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During your early conversations, be prepared to ask more questions and coax the 'whole story' out. If you're too busy listening to the sound of your own voice, you risk missing some important information.

For instance, the shy guy you've set your sights on might be gay. If you're a girl, he'll obviously have no interest in dating you. (Although he might turn out to be a really good friend.)

He's shy, so don't expect him to be shouting about his sexuality. Some shy guys are gay, but quiet about it. Other shy guys are straight, but quiet about it. You'll need to listen (and perhaps directly ask) to establish whether your shy guy is a realistic potential partner.

If he is, then here's some more tips for you.

4. Ask Him Out Away From Other People

If you're starting to communicate but he still hasn't asked you out, be the one to suggest doing something or going somewhere. This isn't the 1950's. Girls don't have to wait for guys to make the first move.

  • Suggest a place where there will only be you two, or few people he can be comfortable with. This strategy can work because it gives him the chance to stay away from the public limelight or any social place.
  • You could ask if he is interested in watching a movie with you at your home. (If you know him well enough to trust him.)
  • Perhaps you're interested in going ten-pin bowling. It doesn't matter if you've never bowled before. In many ways, learning something new together is a great environment for a shy guy. (Bowlers tend to focus on their own lane.)

Don't make a scene or embarrass him. Just ask him out when the two of you are away from other people. A quiet word. A personal text. A private message. Because shy guys generally don't like people knowing their business or being the focus of general attention, you should try to be discreet.

Of course you can tell your friends when you're actually dating. But don't involve them when you're making the initial suggestion to the shy guy. That's a guaranteed way to scare him away.

Make your move in private. Shy guys find it hard to ignore everyone else in the crowd.

Make your move in private. Shy guys find it hard to ignore everyone else in the crowd.

5. Get Physical

There's lots of ways to get physical with a shy guy while still retaining your own personal integrity. You don't have to throw yourself at him. Simply try one of the following ideas ... and then introduce another one. For instance:

  • Don't wait for a shy guy to hold your hand. Instead, reach out and slip your hand into his. Be confident and show him how natural it is.
  • Play fight or jostle him. Get him used to physical touch. Lots of shy guys are not familiar with how it actually feels to touch anyone, particularly a girl they like.
  • Rest your hand on his knee. (Probably not while he's driving the car. lol.)
  • Rest your head on his shoulder while you're watching a movie.
  • Straighten his shirt collar.
  • Brush off his jacket.
  • Get comfortable on the couch, with your legs across him or place his legs across your lap. Any kind of natural, 'getting comfortable' kind of move.
  • Share food with him. Even taking fries from the same container is a sign of intimacy.
  • Kiss him when the time seems right.

Get creative with getting physical. If you're interested in a shy guy, you'll have to be prepared to take the lead. Why? Because you need to convince him you're actually interested in him. Show him how natural and easy it is to be intimate and he'll become more confident with you.

6. Be Comfortable With Silence

If you want to date a shy guy, you shouldn't expect him to be a constant chatterbox. He'll probably become comfortable enough to communicate with you, but he's not likely to have a complete personality transplant. So if you want someone to be talking all the time, don't bother dating the shy guy.

Silence is not the enemy. I've often wondered why so many people it as something that is embarrassing and to be avoided. Make it your friend, and be comfortable with it.

If you're involved with a shy guy, intimacy begins the moment you enter his space. Just being there is 'big' for him. So if you're sitting with your head on his shoulder, holding hands, or sharing a special moment, enjoy it. Smile. Feel happy. Know that you're communicating. Remember the shy guy doesn't necessarily need to talk all the time ... and neither do you. It is perfectly okay to enjoy each other and be comfortable with the silence.

© 2012 Daniel Long

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