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The Secrets to Dating the Shy Guy

Sabrina loves to write about love, life, and everything in-between in a candid yet humorous approach.


Men are hard to figure out. We all know that's a given. They say they don't want games, yet they are the biggest players around. The only thing harder to figure out then a man is a shy man. Forget everything you know about regular guys because the rules don't apply here. Shy guys are the exception to almost every rule. I know this because I have been there. They may seem like a lost cause, but fear not because if you follow a few key rules you are in for a real treat. Shy guys are like a diamond in the rough. It's going to take time and effort, but the end result is totally worth it. Shy guys are some of the nicest, most genuine guys you will ever meet. So if you're not afraid of a little hard work, let's get right down to it.

The shy guy is the exception to every dating rule you know. The exception is the guy that doesn't really fit into any category perfectly. He may not call you after a date, but you shouldn't rule him out just yet because he could still be into you. He's the shy guy that isn't too confident in himself. This is a tough guy to figure out because he may act like he's not into you, but there are certain signs to look out for that prove he is. This is tough because if you come on too strong you will scare him off. It's really tough because you have to express your interest while at the same time not putting too much pressure on him. The key to getting the shy guy is to give him a little nudge and then back off and let him do the rest of the work.

For example, let's say you meet on an online dating website and exchange a few messages. You've seen each others' photos and find them attractive. You have things to talk about and stuff in common. Still, after a couple of weeks of exchanging messages, he's still not asking for your number or out on a date. What do you do? You have to take control of the situation if you want to date this guy. Shy guys don't usually make the first move because they're afraid of rejection. You have to give him your number and then you have to text him first. The key here is to be subtle. Don't text him right when he gives you his number. Wait a couple of days and then text him and just be casual about it. After about a week of texting, every couple of days, throw the bait that you want to meet and see what he says. You have to be casual about it and suggest meeting for drinks. Dinner might be too much for the shy guy right away. After you have set up the meeting you are ready for the next step.

I would suggest meeting in a casual sports bar for drinks. Getting coffee might be a little too casual and if you're just getting coffee, the meeting might end sooner then you want. Getting drinks at a sports bar is just perfect because you can sit and chat in a booth, and if you get hungry you can order appetizers and stretch the evening out further.

Deciding what to wear is also important when you're meeting a shy guy. You don't want to come off as too forward or sexy. I'm not saying, don't show any skin, but just be careful how much you show the first time you meet. I would suggest picking either a low cut shirt and skinny jeans or a more conservative shirt and a shorter skirt.

So here you are meeting for the first time. You already know you have things in common and find each other attractive. The key is to translate that from the digital world of texting to the real world. You don't have to have deep philosophical conversations right away...or ever. Treat the guy like he's your friend. Ask about his day and what he did before meeting. Just keep the conversation going. You will know by the way the conversation is going whether the date is successful or not.

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Don't be quick to mention the word date or ask where this is going with the shy guy. Again, you have to be careful about what you say and how you say it. You might be thinking, what kind of guy is this that would scare so easily? Well most guys scare easily! But the shy guy takes it to the extreme. You have to earn his trust and not come on too strong if you are really interested in developing a relationship with him. He has to get comfortable with being around you and not feel too pressured.

How do you know if the meeting went well? Well, first he showed up didn't he? That counts. If the first meeting lasted longer then an hour then you can be pretty sure he was into you. If it was three or four hours you can be sure he's interested. Think about it...would you spend more than an hour with someone you really couldn't care less about? No, you wouldn't. This is the shy guy's way of showing you he's interested...the time he's investing. This is a guy that won't talk about his feelings for awhile, so you have to look out for other clues to know what he's thinking. Eye contact is another indicator that he's interested in you. I don't know about you, but I don't look at things that aren't interesting, and I certainly don't keep staring at them either. Then you have to look at how the first meeting ended. Did he say he had a good time? Did he ask when you were available next? Those are all good signs to show he is interested.

The shy guy is usually not an experienced dater. He lacks confidence in himself. If you come on too strong you'll just push him away and once that happens it's very hard to get him to come back. The shy guy needs a lot of space and alone time. He also needs time with his friends and he has to know that being with you won't make him lose it. You don't win any points by giving this guy any ultimatums. When you're seriously dating, then you can slowly spend more and more time with him, but still give him space to hang out with his friends. He needs his time to let loose and this way he'll miss you even more.

The most important thing to remember when dating a shy guy is to have patience. You can't rush this because you'll mess it up and it's hard to pick up the pieces with this one. Just take it one day at a time and remember to remind yourself that if the potential is there, you just have to do a few key things to steer this ship in the right direction. Also, remember that the shy guy is still a guy underneath it all. If he's into you, he's into you, even if takes longer to figure that out. What's meant to be will always find its way, and even the shy guy is not an exception to that rule!


Steal Your Heart by Augustana

© 2014 GreenEyes1607

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