Take time getting to know your guy before accepting a date invitation from him. Make sure that the two of you are compatible before agreeing to spend time alone. Strike up a conversation with him to determine his interests and compare them to your own. Situations and conversations can become quite awkward if your guy has much different interests from you own.
Accept the date invitation after concluding that he would make good date material. Agree on a location for your date together. Do not be afraid to place some input into the date-planning process to avoid going somewhere you are not interested in going. If you dislike sports and he takes you to a hockey game, then the conversation could become quite awkward.
Show interest in your guy by attempting to get to know him further. Ask him about his home life, school, work or any other applicable topics. Prepare to divulge to him the same information so that he may get to know you as well. Learning more about your guy will help eliminate much of the potential awkwardness.
Avoid dragging your time together out longer than it should be. There are only so many topics that two people can come up with over the course of a date. Prolonging the date will only slow the conversation down to the point when you may run out of things to say altogether. End the date right when things begin to slow down.
Do not expect to end the date or meeting with a hug or a kiss but be prepared for it if it happens. Lack of preparation may make the mood awkward rather than romantic. Allow him to make the first move but do not show disappointment if he does not.