Tips for Dating Shy Men
One of the characteristics of shy men is that they don’t really believe that women could be interested in them. This is more often the reason that they fail to ask out women, than the fact that they have been rejected in the past. With shy men, it is more a case of getting up the courage to ask out a woman, so sometimes women need to take on more of a leadership role in initiating interest.
Shy men have little self-confidence, so if you are seeking a relationship with one, the first thing you will need to do is to meet them in a place where they will feel at home and display more self-confidence. Maybe he has a favorite restaurant where he goes all the time--if this is the case it is better to meet for lunch or dinner there than it is to just choose a place you like or one you have heard is good.
If he has a favorite bar, meet him there for a drink. Other good places could be a sporting event, a museum, an art gallery, a movie theater--anywhere he will feel at home because he has an interest in that particular activity. If you know for sure he goes jogging every morning before work, if you’re in shape, you could meet him for a jog along his favorite route. This could even lead up to breakfast. Once you have seen shy men where they are confident of their surroundings, they are apt to gain more confidence the next time they are with you.
Another tip for dating shy men is not to delve into his life too closely at first. Some women want to know everything there is to know about a guy before the second date.
This is not a good approach for shy men. You need to go slowly. It is better to stimulate conversation with general questions based on facts you know about him, than to ask very personal questions, such as those about family and friends. Asking a guy if he likes a certain food is less intimidating than probing him about what his family life was like.
In fact, often the reason that men are shy has to do with their upbringing. It may even have been dysfunctional or he may think it was terribly dysfunctional compared to that of his friends or other people he has known. Stay away from family topics until you know each other better.
You can usually never go wrong if you ask shy men for help with something. If the guy thinks that there is something he is good at and that this knowledge can be of help to you, it will greatly improve his self-confidence. Putting a guy in a situation where he feels he can help or fix something is almost always a positive situation. For example, maybe your computer crashed and you have no idea what to do or what is wrong with it. If, for instance, he loves computers and is adept at using and fixing them, he will gain self-confidence by being able to help you out. If he acts like he minds helping, just tell him you will take it to the repair shop and move on to another topic.
Do you best to find out what kind of activities shy men like to do and see if you might both enjoy the same activity or hobby together. Maybe he likes Italian food, or baseball games, or he has a large saltwater aquarium. Don’t pretend you like something you don’t, but if any of his interests are the same as any of yours, make an effort to do something together. He might feel he is an expert at the hobby and that will instill confidence. For example, maybe he loves to play pool and you are not too shabby a pool-player yourself. This is just one of many ways you can find mutual interests which can help you to learn more about one another.