However, because it may be harder for a shy man to interact with women, you could be placing more expectations on the first date than you need to, making the pressure of a first date unbearable. The fear of rejection can render the most confident lion a pussycat, but for the shy it can loom as a larger-than-life challenge that may leave you feeling as stiff as a board. But there are many ways to help manage your shyness as you prepare for the first date. Try these tips to help get you started. Some of these techniques might seem awkward at first, but that’s okay. Do it anyway and, after a while, it will get easier.

• Try dates where you don’t have to talk a lot like a movie or a concert to take off some of the pressure. Sorry guys, no sporting events unless she is an obvious fan.
• Plan dates where there is something obvious to talk about, like a poetry reading or a museum. It will make it easier to keep conversation flowing.
• Remember, she is already there with you. That means she likes you and finds you attractive. She is on your side.
• When it is time to “just talk”, pick the right environment. Restaurants are good, as are parks or skating rinks.
• Stay with it. Shy people tend to think that every little mistake they make is the end; she will never want to see you again. Unless you called her “stupid” or “fat” it is probably a whole lot less of a problem than you think it is.
• If you are at an event, take care of her. Little acts not only make you appear considerate, they also provide a secondary benefit:  When you excuse yourself and return with drinks or food, it gives both the woman and you some time to relax and recover. The contact doesn’t need to be continuous, it just needs to flow.
• Date more than one person. This can be a hard one for the shy, but the main reason it is so hard for you is that you don’t do it enough. Don’t invest all of your sense of self in the success or failure of one encounter. Talk to more women, even if you are not interested in dating them. Strike up a conversation in line at the grocery store or at the post office (where you always have a lot of time).
• Remember your successes. Remind yourself of them always. Shyness of mind reinforces the tendency to overlook one’s successes and concentrate only on failures.  Pay attention to what works.

Remember — Being shy is not a defect or a fatal flaw. There is nothing wrong with you! Everyone feels self-conscious when they try to do something for the first couple of times. Remind yourself that there are plenty of people in your life who do like you, and like to be around you. And there are many, many people who would be very happy and feel very blessed that you were in their life. Give them a chance to meet you.