Asking someone out may be easier if you plan in advance what you are going to say specifically. Say, "You want to have Chinese food or Italian food? I know a couple of restaurants that serve this excellent cuisine." You form an idea of where you would like to go on the date and she can visualize how the date will be like if she does go out with you. It's a good idea to ask the person only when he or she is alone. You will be red with embarrassment if you do ask her when she is with her clique. Yeah, Harry Potter made that mistake when he asked Cho Chang out, but he was still a boy at that time!
Get a reality check, it is hard to ask someone out on a date(unless you are so thick-skinned). Harry Potter did make himself vulnerable and risked rejection when he asked Cho. After all, the girl of your dreams might say no. But she could say yes, too! This is when I ask more men to indulge Nike's slogan, practically.
Just Do It.
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