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What To Wear On A First Date If You're Not 20 Anymore

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27. Wear A Flirty Jersey Dress
For those who want to be flirty but want to reserve the wiggle dress for the third date, try putting on a jersey dress instead. The soft material is still sensual, and it still clings to your curves but in a more casual way. You can also dress it up with accessories, like elegantly wrapping a scarf around your neck.