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The Only Things You Should Have in Your Pockets on a First Date

Preparing for a date can be a stressful time, but anxiety is no excuse for having a South Park wallet when escorting a young lady around town.  Here’s what to hold on to and what to ditch.

By Sydney Pendle

It’s your night, friend, the world is yours. Whether you are a spunky young gent looking to sink his teeth into the world of post higher education adult dating or a seasoned veteran going up to bat in what seems like the 50th extra inning, we can all agree that dating carries a certain weight on all of our minds. There are a lot of questions to ask ourselves about what we will wear or where we will go.

However, one thing that you may not always ask yourself is, “what do I take with me?” This is a very important issue that often goes overlooked. In this world of gadgetry and mobile, well…everything, it’s hard to know what to take and what to leave and where to leave it. We need to know what to bring because we don’t want to be without something we need, but if we bring too much then we look both bulky and out of place. You have to be ready, but you aren’t a boy scout.

Just follow these few guidelines and you will be all set to go.

What to Bring:

  • A well kept wallet
  • Cell phone, sans the belt clip
  • Keys
  • Cigarette case (if you smoke)

What to Leave at Home:

  • Gum and mints
  • The expired condom in your wallet
  • Your trusty messenger bag
  • Your collection of electronics
  • Most everything else

It is customary for a true gentleman to pay on the date regardless. Bring the wallet and have a good amount of cash on you. It’s always important to have a well-groomed wallet. I doubt that she will be impressed with your grocery store supersavers membership or your 5 maxed out credit cards. Have your ID, enough cash ($50-$100), and your debit card just in case.

Be sensible, not George Costanza.

And look at the state of your wallet. Does it have a skate logo or cartoon character on it? Time to upgrade to a big boy wallet, friend. It doesn’t have to be crazy expensive, just something simple and classy. 20 bucks at a Wal-Mart can solve all your problems. And lose the condom. Not only because it’s going to disintegrate when you open it, but also because a gentleman does not take a woman to the bathroom of the restaurant they are in on the first date.

If you need to get one, make a quick stop at a 24 hr place and pick one up, no biggie. Any smart modern girl who is willing to have sex with you that early will probably have a few back at her place and vice versa.

Dates, especially first dates can be filled with excitement and wonder or absolute misery. But a true gentleman does not simply bail on a woman because she is homely or a dullard with no good reason. However, nobody said anything about not having an escape plan.

Keep the cell phone with you for that “emergency call from work.” Try to remember what you have told her already… if you have already admitted that you work in the mailroom of a law firm, she will doubt you actually have an emergency call from work. Maybe having a code word you can quickly text to a friend who can fake call you.

Otherwise just keep the phone in your pocket. It’s very rude to text or email when someone is trying to talk to you. And by keep it in your pocket, I don’t mean on your belt. This isn’t 1999, guy. If you are going on a date with your girlfriend or wife, consider leaving the phone in the car. Nothing says “I love you” like a simple gesture that shows you are ready to listen and talk to just her for the night.

As for the gum and mints, it’s nice to have fresh breath, but let’s be realistic. You have gotten all gussied up in your finest duds; you’ve put on a hard shoe, a black sock and nice pants. Now you’re going to ruin it buy having a weird shape in your pants that rattles every time you take a step?

Remember less is so much more. If it’s a worst-case scenario, have a Tic Tac or two stashed in your coat pocket. Or if you need to freshen your breath, just ask your date. She will probably have something in her purse and if not, just keep some in the car.

Keep in mind: a gentleman doesn’t chew gum in front of a lady, and while that custom may seem outdated, it’s still rude and unattractive on a first date.

The hardest thing a lot of guys deal with is how to break the fact that they smoke. What better way to do so than with an apologetic confession and taking out your classy silver cigarette case and lighting up a Lucky Strike? The case is perfect for holding a small book of matches and a few smokes. You could also opt to put those breath mints in there if you really have to. But remember that they are in there, because if you go to open it and little pill looking things come spilling out, kiss (or probably don’t kiss) your date goodbye.

As for everything else, there are just a few things to consider. Leave the bag at home, you aren’t at a business meeting. Leave the camera at home, you aren’t at the prom.

Like I said men, it’s a tough subject but just remember less is more. Keep it simple and remember just bring your confidence and your gentlemanly tendencies and you will be fine.

Sydney Pendle is an up and coming blogger from Seattle.  Check out more of Sydney’s writing at his blog bymennon.com

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