Any flirt will tell you: A good pickup line said at the right time can be a great conversation starter. But how do you come off clever and not clueless? The trick to pulling off a pickup line is never taking it seriously. You want to show off your charm and wit with a wink. You want to make the person laugh, not cringe. And you want to say it with breezy confidence—yes, that’s a thing—so practice with some of these.