First – two deadly questions not to ask: Do not ask, “You want to go out?” it’s too open-ended and can lead to awkward follow up conversation. Do not ask, “What are you doing Friday night?” It’s too vague. It may leave your potential date wondering exactly what you have in mind. The other person doesn’t know if you’re just curious about what she/he is doing on Friday night or if you want to do something with them.. Try something along the lines of: “You like to rollerblade? I was thinking of going out to the lake on Saturday. It’s great out there. Would you like to go with me?” Or if you’re really uncertain or uncomfortable about getting together – go with a group. Ask the question: “Hey, there’re a bunch of us going bowling on Saturday. Would you like to go?” The operative word here is “us.” It immediately takes the pressure off. Planning activities to do on your date and getting together in a group are good ways to go – especially if you think you or your date might get “tongue-tied.” If you’re busy or there are a bunch of other people in the conversation, you won’t hit awkward silences and won’t have to talk all the time if you don’t know your date very well. In summary, just remember when you are asking someone out: 1) Plan ahead Know what you are going to say AND what you want to suggest to do on the date. 2) Be specific The other person will be much more comfortable if they know exactly what your intentions are and what you want to do. Try to relax and enjoy yourself – worst case – they’ll say they can’t go out and you’ll find someone else who will. Someone who appreciates you. In other words, if the person you are asking out doesn’t have enough insight to recognize what a terrific person you are, then they’re just not too bright now, are they?