So you’ve got a date. Congrats, you’ve navigated one of the hardest parts of the (now almost entirely online) dating landscape and are embarking on the next hardest part: the first date.
Getting ready for your date will set the tone for your interaction, so it’s important that it goes smoothly. Even though “getting ready for a date” may just sound like mere grooming and outfit choices, there are many more things that go into it than that.
Before we dive into how to get ready for a date, we often get questions about dating, social etiquette, and conversation in our increasingly digitized world. The fact is that all of these activities are tricky and don’t have a set formula for success. Our main recommendation is to check out our article on What It Means To Be A Gentleman Today. It outlines the actions of a man who wants to be defined as a gentleman, which is something you have to decide for yourself.
If you enjoy the Gentleman’s Gazette, we assume that being a gentleman is something that you strive for. As such, if your goal is simply to get laid, this isn’t the guide for you. This guide assumes that as a gentleman, you are interested in making a legitimate emotional connection with another human being.
Like many things in our society, the rituals around dating have become increasingly casualised and hazy. The old formula – meeting in person, arranging a date on the phone, picking her up – is long dead, and has been replaced by mostly digital communication. The emotional risks are a fraction of what they used to be, but as a gentleman, you shouldn’t be afraid to face those head on.
Online dating alone has massively expanded the pool of people you can choose from, and that has shifted attitudes, often negatively, about the belief that there is always someone else to date if one doesn’t work out. Rejection is no fun, but neither is being on a date that the other person clearly doesn’t take seriously. As such, this article assumes that you take dating seriously, you’re a grown man and you embrace acting like one.
Without further ado, here is our guide to successful date preparation:
The Week Prior
First of All, Make it Clear it’s a Date
Even though it seems like that would already be clear since you’ve agreed to meet in person, the vagueries of internet dating have made it so that someone looking for a hookup or a real date can sound frustratingly similar. It’s hard to know what the other person’s expectations are going in, but at the very least you can make yours known. It can be as simple as saying “it’s a date” after you agree to meet. It’s a little word, but it can go a long way to show that you’re not afraid to say you want to explore the romantic possibilities between you.
Make Plans Together
If you haven’t already made plans, contact your date to make plans together. Come prepared to the conversation with some ideas, but the classic date is dinner at a restaurant. If your date prefers to meet for coffee or drinks for whatever reason, then follow their lead, but otherwise don’t be nervous to suggest a couple dinner options.
I recently read an article that claimed that dinner was a bad first choice for a date because it created “too many expectations”. Suggesting that a grown man can’t handle the pressure of choosing a restaurant, making a reservation, getting to know someone and managing the awkward check paying? If that is the new standard for dating, they have gotten shockingly low. You can do better. If your date is amenable to dinner, suggest a couple places that are conducive to conversation and volunteer to make a reservation. Your willingness to make an effort won’t be lost on your date.
Get a Haircut
You probably get a haircut every 4-6 weeks anyway, so now is a great time to schedule a trim.
The Day Before Your Date
Your time is valuable, and so is your date’s. A quick text to say you are looking forward to seeing your date the following day gives you both an opportunity to update plans if needed.
Even though it may seem like a classic gentlemanly move, don’t offer to pick your date up if it’s the first time you are meeting in person. If you date goes well, you can certainly make that offer for the second date, but it’s still a wise idea to make sure both you and your date can exit on your own terms if it doesn’t go well on the first date.
Choose a Great Outfit
Your outfit should showcase your style and make you feel confident, but it should also suit your venue and the likely clothing choices of your date. In general, a gentleman’s style is more formal than the average guy, but this is one of the rare cases in which we don’t recommend wearing something dressy like a suit or even an odd combination. In the US, women almost always dress more formally than men when you consider the efforts they put into hair, makeup, clothes and high heels, so you still want to aim for a casual but considered look.
A blazer or a sports coat is a still a good choice, but consider pairing it with more casual pants such as chinos or jeans. Skip the necktie and simply wear it with a neatly pressed collared shirt and a great pair of brown leather shoes and a matching belt. Accessorize with a pocket square and a watch. For a more youthful look, choose a checkered shirt rather than a plain one.
In the cooler seasons, you can wear a tie with a collared shirt and a v-neck sweater in place of a jacket. For warmer seasons, opt for just a collared shirt but avoid shorts, sandals, and t-shirts. If your choice of venue is too casual for a jacket, skip it and wear either a polo or a collared shirt with pants. Even though sneakers are popular today, we’d still recommend opting for casual shoes such as driving mocs or loafers over sneakers (even new, clean, stylish ones) on the first date. Alternatively, if you are coming directly from the office, take 2 minutes before leaving to de-corporatize your look by removing your tie, jacket or both, and swapping out your pocket square for a more playful one.
Once you’ve chosen your outfit, make sure to touch up any shoes that need polishing or shirts that need ironing, so you look your best.
The Day of Your Date
You want to look your best, and grooming for a date is equally as important as what you choose to wear. Trim your beard if you have one and if not take the time to do a proper double-edge razor shave if it’s not already part of your regular routine. Shower, brush your teeth, clip and file your nails, and apply cologne with a light hand.
Check Your Wallet & Think About Payment
Make sure you have everything you need in your wallet. Have a little cash on hand for valets, parking meters or ramps, tips or games you might come across, as well as your ID and a check card or credit card with enough money on them to cover your needs for the night.
That begs the question of how you will handle who pays for what on your date; it will be less awkward to deal with it if you give it a little forethought. To make matters worse, if you ask 10 people their position on this question (men and women alike) you’ll get 10 different answers. That being said, it’s no longer an absolute expectation that the man will pay for the first date, so it’s best to be prepared to navigate a variety of possible scenarios. We’d argue that it shouldn’t matter who asked who on a date since as adults you both agreed to meet. When the check arrives, don’t let it linger awkwardly at the edge of the table. Someone has to open the conversation, and hesitation will only make things worse. In general, we still think it’s a good idea to offer to pay for dinner and gauge the response. Don’t wait for your date to go to the bathroom, override them if they insist on paying for themselves, or suggest they pay for something else. While it’s important to not let the paying conversation devolve into an awkward standoff, you shouldn’t strip your date of the right to participate in making the decision. Furthermore, the first date is just that – one evening or outing together. How you agree to pay for it does not need to set the standard for who pays on future dates.
Review What You Know
A friend of mine was saying their goodbyes after a first date when their date said “I had a great time and would love to see you again. What’s your name again?” You can probably guess how many dates happened after that fateful moment.
With the prevalence of online dating and extensive dating profiles, most people have a lot more access to information about their dates than when it all had to happen the old fashioned way. Before you head out on a date, take 5 minutes to review the person’s profile, your messages, and any other written correspondence you might have had. You’ll avoid the embarrassment of covering the same topics twice, and you may find new things to ask about in case there is a lull in the conversation.
If you feel like getting to know someone isn’t your strong suit, check out our article on 53 Questions to Ask to Get to Know Someone. Keep a couple of those questions in the back of your mind if you should need one of them.
Then, put your phone on silent, tuck it away, and head out the door – don’t be late!
Dating isn’t easy, but like most things, prepping in advance can alleviate a lot of the in-the-moment stresses that can come up on a date. How do you prep for a date? How do you handle awkward moments?