A gents guide to a first date (that helps you land the second one)


First impressions are important. We can’t stress that enough. That goes for job interviews, but that also very much goes for your first date. If you’ve managed to convince a cute girl to have a date with you, the last thing you’ll want is to dress inappropriately. You don’t want to loose her, now you have her on the hook, do you? Follow these dating tips, and you’re sure to land a second one.

Where do you take her, what do you wear, how early do you show up, how long do you wait to call her afterward… the list of thoughts goes on. You are probably getting more nervous by the hour that approaches your first date.

When it comes to dressing however, and how you should act on your date, we’ve got you covered in this article.
You’ll want to do everything that you possibly can in order to land the second (and third, and fourth) date, right?

Here’s our official list of first date tips so that potential second date in your future becomes a reality.

How to Dress to Land the Second Date:

DO make sure to put some real thought into your chosen outfit. Men know whether or not there’s long-term potential for his partner within the first few minutes of meeting her – and the same goes for women. If you normally wear washed out jeans, T-Shirts and flip flops – you’re in bad luck. There’s none of that for the first date. You need to dress yourself in a way that sends her a message that you take her (and her time) seriously, and that you put some thought into your time together. It only takes a few seconds for someone to form an impression of you, as we already mentioned. Before you even say “hello,” she’ll be sizing you up.

That may sound intimidating, but it is a true statement of all of us. Appearance and first impressions are crucial.
Even if you end up not working out after the first date, she won’t be able to look back on your evening together and make judgments about your lifestyle (slob living in his parents’ basement, most likely) based on your appearance – because you’re going to look damn good. Right?
And if you do end up working out together, the good first impression you’ve made never hurts. It’s a win-win really.

DON’T wear a suit. That is, unless you plan to take her to the opera and a fancy restaurant. Don’t reach for that suit in your closet and think that it’s a safe choice. It’s really not. Not always. Although we do love and craft custom-tailored suits – when it comes to the first date, you want to appear like you know how to dress yourself, but you don’t want to come off as uptight. Nobody likes a guy with a stick up his buttocks.

Save your suit for work and extremely special dates, and stick to a more casual, yet still refined look.

DO wear a collared dress shirt or a nice sweater, or both. Make sure that your clothing choices fit well, too. Stick to darker colours and neutrals for a classic look. Also, make sure that everything is clean and pressed.

DON’T wear a tie. Unless the place you are taking her requires a tie as part of their dress code, feel free to skip the tie. Save it for the next date, after you’ve gotten to know each other, so your first impression isn’t “overly dressy.”

DO make sure to choose your accessories carefully. Stick to the classics. A nice watch, a leather belt, and good socks should do the trick without overdoing it.

DON’T overdo the cologne. Sure, you probably have that one signature scent of yours that you whip out for special occasions – which is great – but keep it subtle. She’ll notice the scent without you needing to pour a questionable lot of it down your neck.

DO wear amazing shoes. What you’ll come to realise is that women are obsessed with shoes–both hers and yours. So, opt for the cool boots, some nice chukkas, or down that route. Your shoe game should be strong, because it will be one of the first things that she’ll notice, without a doubt.

Casual shoes (boots, chukkas, nice sneakers) are fine for daytime dates, and for dates that take place after dark, reach for some lace-ups, loafers, or nice boots that don’t appear worn out. Keep the flip flops at home for the first date unless it’s at the beach.

DON’T do something new (i.e. that you’ve never attempted before in your life) – with your hair!
Don’t try a new hair style, and definitely don’t suddenly get a new haircut the day before.
This is a catastrophe waiting to happen, and must be avoided at all costs.
Instead, stick to your usual grooming routine. After all, why change up the hair that helped get you the date in the first place? Right?

DO be well groomed and clean! Always. You’d be surprised how quickly a woman will notice these things. Women are all about the details. Make sure that your nails are filed, your hair is clean, you’ve taken a shower, you’re wearing deodorant, and that you’re cleanly shaven or “cleanly rugged.”

DON’T wear a baseball cap. Ever. Please. Unless you’re going to an actual baseball game, in which case, by all means – if you can’t resist.

DO wear a jacket, if appropriate. Layers are always good, and at the end of the night, if she’s cold, you can offer her yours.
Classy. Gentlemanly – and it shows that you’re caring!

How to Act to Land the Second Date:

Your appearance is just 50% of the equation. The other 50% depends on you not only looking like a gentleman, but also acting like one!

A classy woman will appreciate a classy man – that much we can guarantee you.

DO arrive at the destination or at her house early. She will most likely be running late, but that doesn’t mean you should do the same. Never be late to your date.

DON’T berate her with questions, but instead…

DO ask her questions and make sure to hold a steady conversation. Women love to talk, and women especially love when you take a genuine interest in their lives, backgrounds, and aspirations. When talking, try to follow a one for one rule. When she asks you a question, take it as a silent cue that it’s appropriate to ask a similar question back after responding.

DON’T leave your phone volume on. In fact, try not to check your phone at all. Leave it in your pocket on silent and keep your attention focused on your time together. There’s time to check your Facebook status after the date.

DO be nice to everyone. She will notice if you’re rude to your waitress, or say “excuse me” when squeezing past people to reach your seat. Your attitude will be viewed as a reflection of the way you would potentially treat her, so be mindful.

DON’T let her go Dutch! At least not on the first date. If you were the one that asked her out, expect to pay for the date and grab the tab immediately as it arrives at your table. If she insists on paying, kindly decline or offer to go Dutch on the next date (Subtle, huh?). Feel free to go Dutch on all other dates afterward, but keep it old school on the first date – and wine and dine her to her heart’s content.

DO tell her that you had a great time, and initiate conversation after the date. It’s pretty hard to say which women believe in the “Two-Day Rule” and which think it’s madness. A safe bet is to thank her for the date and tell her that you had fun either later that day, or first thing on the next day. Leave the ball in her court after that.

You’ll have initiated conversation without being too forward, and it will be up to her after that to decide how soon is too soon to start discussing that second date.

And there you have it, gents!
Prepare your attire and your attitude in advance, and once the time of your date arrives, forget all your worries, and enjoy your time together. Knowing that you look good and are acting appropriately will give you the confidence you need to trust your gut, and focus on the woman you’re with.

She’ll appreciate your effort, and you can go forth and get to know one another in what should be an amazing evening (or day).

Good luck, gentlemen!