What to Carry on a First Date: The Gentleman's Arsenal

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The First Date with a woman is your chance to display your charming and chivalrous side. While most acts of chivalry (like opening a door for your date or helping her to her seat) require only your thoughtfulness, moments will arise when you’ll need a tool to assist in your kindness. Below I’ve included a short list of items I recommend a well-armed gentleman having on him during a first date (or any time for that matter) that will prepare him for any situation and leave his date impressed.


Before you head out on your date, slip a clean, pressed white hankie into your pocket. When your date tears up during the movie you’re seeing, she’ll appreciate the offer of a soft hankie. Hankies can come in handy in non-crying situations, too. If your date gets grease or food on her clothing, give her your hankie so she can clean herself up. Let her keep it when she’s done with it. First, it might have her snot in it. Second, when she does get around to washing it, your hankie will serve as a reminder of how awesome you are. She won’t be able to wait to go on a second date with you.


Nom nom nom. That garlic infused steak topped with garnished onions was delicious. But now your breath reeks to high heaven. Trust me. Your date doesn’t want to smell what you ate for dinner the rest of the night. Show some courtesy by popping a few mints as you step out of the restaurant. You’ll only be increasing your chances for that first kiss. Your date will probably be looking for something to freshen up her breath during the date as well, so make sure you’re prepared when she asks if you have anything that will do the trick.

“Everything had its own little home, neat and tidy. The white linen handkerchief on the inside pocket. The little mints… A single key on a fob.”

~ Nancy Sinatra on the contents of Frank Sinatra’s pockets

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