New clothes are often uncomfortable, and can unexpectedly bunch, rip, or gap. Besides, why add the worry about spilling red wine on your new outfit to the other stress of a first date? Why worry about clothes when there are more important things to worry about, like the broccoli between your front teeth or whether your date really likes you or is just being polite. Wear your happy, easy-to-wear, good luck, appropriate-to-wear clothes. If I ran the world, I’d make sure that on first dates, everyone would wear his or her oldest, most comfy clothes; women would not shave their legs; men would not buy new after-shave; and all men and women would be who they really are, right from the get-go. Obviously, I’m not in charge. Shoes should always be shined, cuffs unfrayed, and everything neat and clean — not rigid, new, starched, and impressive.
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