Never say, “Would you like to go out sometime?”

If you phrase the invitation like this and the askee says “no,” you’ve left yourself absolutely no out except to be swallowed up by a prayed-for earthquake. If the person says “yes,” you still have to ask him or her out. Yikes. Instead, be specific. It’s much better to say, “I’d love to see the new exhibit at the museum. Any interest in going either Wednesday or Thursday?” You offer a specific opportunity (as well as alternative days) and at the same time, you give your potential date a great deal of room in which to negotiate without sounding wishy-washy or desperate. Giving specifics also allows your potential date a couple of seconds to think about it, rather than getting caught completely off guard.