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Posted on 08 December 2019


Ah, the first date. They’re kind of a beautiful thing. What to wear, where to go, what to say? They’re kind of a really hard event to plan for. But, like any situation in life, with the right side pieces in your pocket, you can take on anything, right? Not exactly. But a man can try, and that’s the most important part. With the following accessories in your inventory, you might just make that evening special for the both of you and, here’s to hoping, even be lucky enough to land that second date.

Here’s 5 things a man should always carry on a first date:


Nervous hands can make quite a mess, from sweaty palms to a little spillage. This is when a simple handkerchief or pocket square comes in handy. No one enjoys sitting at a wet table or with sticky hands. A handkerchief can simply wipe that mess away (or those palms) and ensure your night keeps going smoothly. Aside from being a hell of a lot more eco-friendly than paper serviettes or napkins, it’s actually the perfect accessory for a back pocket or a blazer.


We’ve all seen it in the movies and although we don’t exactly recommend chewing on your toothpick in front of your date, we do recommend keeping one or two in your jacket pocket. Let’s be honest, we’ve all had something get caught up after a meal from time to time. It’s an uncomfortable feeling, and it can make us feel self-conscious to the point where we’re afraid to smile or annunciate our words in case our date sees. This is when a little oral care can go a long way. From a simple breath mint to floss, chewing gum or even a toothpick, it’s an excellent way to freshen up and make sure everything is intact.


Ever heard that laughter is the best medicine? Well, it’s also a great ice breaker. In our own experience, making someone laugh has gotten us through tough talks, situations and even conflict. It’s great to be a little humorous, and better yet, the ability to poke fun at yourself shows one’s modesty. Don’t tear yourself a new one trying to make your date laugh – you’ve got a number of great qualities we’re certain your date would love to hear about. Do: have a little fun with your words. Weaving information into your words or jokes can help you introduce yourself without coming across as self-absorbed when done correctly. Remember, like anything in life, there’s a line to draw. A good balance of cheeky and serious will do you wonders.


If you’ve seen our other stories in our 5 To Carry series you’ll know we’re adamant a man should never leave home without his wallet. On a first date, well, we take that another step further and say that wallet better carry a little dough in it. There’s a number of reasons to carry cash on a first date and they’ve got nothing to do with appearing flashy. Cash can solve a number of problems from splitting the bill to a broken down Eftpos system. It’s handy when you want to tip and ensure it goes directly to employees and, on the rare occasion, some restaurants even offer small discounts for customers paying in cash.

Fun fact: Australian bank notes, made of polymer, are some of the most advanced in the world.


In line with the theme of the series, it’s always nice to be a little prepared in life. A back-up plan isn’t necessarily a reconnaissance mission; you don’t need to know the lay of the land, or, you know, bar, restaurant, market or wherever you choose to go. It is nice, however, to take a look at places nearby and know your options. That handmade pasta joint in Fitzroy is fully booked? No problem, there’s actually a really cute tapas bar just down the road. Dinner’s over, but the conversation isn’t? Easy, you’ll know there’s an incredible speakeasy just down the road where the cocktails are made to order.

That last to-carry option is actually a great little point to keep in mind in case the date doesn’t go according to plan. While we’re not saying, you need to rehearse a ‘we might be better as friends’ speech, having an idea of what you might say can help that process move smoothly. If things do turn out well, then well done, we wish you all the best.

Have a few cheeky date hacks of your own? Let us know below. We might even try them ourselves next time.

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