#29: Not the Right Time or Place
Asking someone out should be a private matter, and there’s no need to make it awkward from the start. If you’re going to take the chance and ask someone out, consider the right time and the right place. You probably wouldn’t ask someone out with a large group of friends, but there are other places you should avoid, too.
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No matter what you do, do not ask someone out while they are on the clock. Not only are you putting them on the spot, but you’re also making it weird for all of their coworkers. You stand a much greater chance of making a good impression if you wait until they live on their own time.