How to Prepare Yourself (And Your Wardrobe) for a First Date

Are you getting ready for a first date?

This can be understandably nerve-wracking! Where should you go? What should you do? What should you wear? And if you’ve been out of the dating game for a while, how does dating work in this day and age?

Phew, it’s a lot to take in and one thing we will say is don’t be nervous! Whatever happens, will happen, and we’re great proponents of “if it’s meant to be, it will be.”

That said, we think a first date is a great opportunity to put yourself out there and meet someone new – whether that be a friend or something more. There’s no harm in doing a little preparation, in fact, that’s good practice!

Here are some of our tips for preparing yourself:

Modern dating etiquette

With dating apps and swiping right, it can be a confusing minefield to understand dating etiquette. The good news is, while some things have evolved, the very basics remain the same. For example:

1. Be authentic! There’s no sense in pretending to be someone you’re not in an effort to impress someone. Represent yourself honestly for the chance of building a genuine connection with someone.
2. Show up on time. Being late communicates that someone isn’t a priority to you.
3. Take pride in your appearance. Be dressed nicely and well-groomed!
4. Ask about any preferences or food allergies. There’s no sense in booking the cool new sushi restaurant if your date is allergic to seafood.
5. Make sure you have cash in your wallet. It’s not that the man always has to pay for everything anymore (you might choose to split the bill, or whoever suggested the date pays), but having cash is important in case of things like cards not working or some kind of outage meaning cards can’t be used. Having cash can save you from an awkward situation…
6. Be courteous. Manners never go out of style!
7. Practice being a good listener! A common mistake that some people make is to be so busy trying to impress their date with their knowledge/wit/prowess/importance that they don’t really listen. This means letting your date finish before chiming in and making sure you really understood. For example, you might paraphrase what they just said or ask clarifying questions.

There are a few more things to add here of course. One is that if there’s someone you’re interested in, approach them! Life is too short for any sort of gamesmanship – strike up a conversation and see where it takes you.

Another important consideration for the modern era is the ubiquitous mobile phone. There are so many tales of people ignoring each other to bury their faces in their phones that not picking up the phone during a meal has become a popular challenge.

We have a couple of suggestions here. Firstly, don’t pick up your phone unless you know it may be urgent (for example, someone close to you is in hospital, or someone is calling who wouldn’t call unless it was urgent). Even then, it is good manners to explain that to your date – you’re not pausing to chitchat, you’re dealing with something important.

Secondly, put your phone on silent so that you’re not tempted to check every buzz and beep. Give your date your full attention – being distracted by your phone for non-urgent reasons is just rude.

On a first date? Good manners are never out of style Share on X

Make considered plans

It’s important to make considered plans for a first date. The aim should be to get to know someone in a setting where both of you will be comfortable. This means that it’s generally best to pick a neutral, low-pressure sort of place.

For this reason, places with a casual vibe, like a hip local café or a new brew pub can be a good choice. If the situation feels uncomfortable, it doesn’t have to last long in those places, whereas at a fine dining restaurant you may be awkwardly stuck through the next three courses.

To be extra-prepared, if you’ve got somewhere in-mind, check it out ahead of time to see what the atmosphere is like. Buzzing with people can be good, but you don’t want the noise levels so loud that you won’t hear one another.

If you’re often nervous or have social anxiety, it can be helpful to think of some good conversation starters before your date. Studies show that women in particular rate cheesy pick-up lines and empty compliments poorly, whereas someone who sparks interesting conversations can show they are intelligent and genuinely curious.

Importantly, be in the right mindset for your date. If you’re filled with self-doubt, that tends to show up and cloud your time. Practicing “self-compassion” has been shown to improve the outlook of your date. This means that instead of focusing on past dating experiences that didn’t go well, you acknowledge that frustration over dating is part of the shared human experience. The nervousness or fear you feel ahead of a date isn’t a sign that something is wrong with you, but is a common response among many people. You go into your date with the hopes of it going well and having fun.

Dressing for your date

We’ve had many gentlemen in, shopping for first date outfits. There always seems to be a mixture of nervousness and excitement. One thing we suggest is to be cognizant that you may sweat. Meeting someone new can be nerve-wracking and induce sweating, so it’s important to be mindful of this when you pick your outfit.

For example, you don’t want to wear a shirt that will show your nervous sweat stains around the armpits. Try a moisture-wicking shirt instead – there are both dress shirts and casual shirts that meet this description. Something in navy blue or even a bold print will also tend to work to hide sweat. We are currently preparing a Spring Collection of shirt styles that will update your wardrobe in fit, patterns and fabric, including moisture-wicking options.

A second thing we always suggest is to wear something that is both comfortable and appropriate for the date activity. If you’re going bowling, wear a nice casual shirt that you’ll be comfortable playing in. If you’re going to a nice restaurant, choose an outfit that you feel fits in well with the setting.

Third, think about fit. Don’t try squeezing into those trousers that barely fit anymore – this could be a recipe for an embarrassing incident! Wear clothes that fit you well without being too tight or too loose.

Importantly, wear something that speaks to your own style! If you enjoy wearing an eccentric Paul Smith flower shirt, wear that! If you are more into Peter Millar, go for it because if you’re comfortable in what you wear, you will be comfortable with yourself on the date.

Here are some outfit suggestions below:

Final thoughts

Clean, tidy and well-groomed are always the right choices when it comes to a first date. Pay attention to the cleanliness of your shoes and overall tidiness of your clothes. Use a lint roller to remove stray fluff, replace any missing buttons and trim loose threads.

Of course, if you want to look extra-smart, go for a tailored outfit! Made to fit is always a flattering choice. We at Family Britches are happy to help!