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What Do Girls Look For On A First Date? The First Impression Stuff!


  • What is Most Important During a First Date?
  • 11 First Impression Tips
  • What do women remember about their first date?
  • How outfit designer online can help?

So you have decided to enter the dating world, and you are about to take this girl out on your first date. How are you feeling? Nothing beats been prepared for success. Here at Winslow, we work in image consultancy, that first impression stuff where we design the best outfit for men. It is perhaps your most powerful tool in starting the date on a positive note.

Did you know that first impressions create a subconscious judgement or the tone of experience? It is much harder to change a mind once they have a subconscious belief or judgement about you.

The below table highlights what is most important to both Males and Females on a first date. In the order of importance.

What is most important during a first date?

Here are our First Impression Tips

1. Show Up

Show up in many ways, not just on time, but with your attention and being present all throughout the date.  We hear you saying to yourself the whole “fashionably late” conversation, but on a first date, you make a better impression if you are on time.

Showing up also means being present, with complete attention and focus on your date. This is something every girl is looking out for, There’s nothing more insulting for a woman than to see her man staring at other women. Be present and be at the moment, with your date.

2. Shoes

Any remotely discerning woman would glance at your choice of footwear and attempt to read it, whether or not her conclusions reached are just, this will influence her impression of you.

Make sure you do look at the shoes that you are wearing, avoid running shoes, anything over the top, or your work shoes. Wear something clean and comfortable, if in doubt keep it simple.

It is a simple thing to do, but it is the most forgotten little detail that guys leave out when dating.

3. How You Dress

How you dress and express yourself is a turn on for women too, you don’t have to be over the top just need to be authentic and know how to express your personality through your clothing by choosing the best outfit for men.

Whatever attire is appropriate it is nice for the man to make an effort in his appearance. Be pleasing to her eyes, isn’t this what we guys look for too.

Obviously, you want to look your best, but a first date isn’t the time to take those new style risks, when you are with her on that first date it is anxiety-filled anyways and hence be stylish but be comfortable in your clothes, there is no need to add more complexities to the situation.

At Winslow, we pride ourselves on self-expression. We also understand that the journey of discovery and expression is a journey, that continues to evolve.


If you have not discovered how to express yourself through clothing, why don’t you take action now and give us a call, let’s do coffee?

4. Cleanliness

Yes, you should shower before your date. This is not optional. You definitely need to be clean. Give your nails a clip and get rid of any gunk that may be residing underneath them.

If you have the time even go get a manicure, why not? It couldn’t hurt.  Some women will consciously look at them, while others will do it without even realizing and process the information subconsciously.

5. Groom Yourself

Get a haircut! There are several people that say that you, “never” go for a hair-cut on the day of or day before your date, just in case they stuff it up. Depends, if you are getting a full on do, then maybe it is not the best idea to bring it out on your first date, when we mean a haircut we mean a touchup, specifically around your neckline, to make you look and feel fresh and new.

Clean up your beard, and highlight your jawline, and shape the beard to the contours of your face.

A groomed beard is a message that you are telling your date, that you know how to look after yourself and will not be a burden. Subconsciously our minds are thinking compatibility.

Prune the other odds ends such as ears, nose, brow, back, and down there if you must. Bringing out your A-Game will mean a better chance of success for a second date.

6. Freshen Up

When you meet a girl, do you shake hands, hug, or go for one of those awkward cheek kisses?

Whatever is your style, you don’t want your date to get a whiff of your unpleasant odour, if it is not favourable and not a great first impression.  Make sure you apply a spritz of choice well ahead of time and make mouth stink disappear before meeting her, just don’t overdo it.

7. Put Your Phone Away

In the modern world, our phones have become an extension of our lives, everywhere we go, in the trains, on the walkways, in bars and in social scenes it is common to see people glued to their phones and missing the world around them.

The act of obsessively checking your phone every few minutes is a definite deal breaker on a date. There is nothing more annoying or rude than trying to have a conversation with a person who is constantly checking their phones.

Whatever it is, it can wait, be present for your date, if the matter is urgent then excuse yourself and deal with the matter. But checking your Instagram pics, or your emails is straight out failure on a first date.

8. Conversation

Now that you have had the courage to ask the girl of your dreams on a date, and you have approached the situation well prepared and with your best foot forward with a great first impression, the rest of the experience is up to you and your compatibility of values and interests.

For women, conversation is ranked and the most valued attribute in seeking a compatible partner, even more than looks. So brush up your conversation skills, a foolproof way to ensure conversation will always be flowing is to simply ask questions, keep it semi-general until you are both comfortable to tackle the big stuff like religion and exes.

Be open to learning new things not only about each other but also about the world. While it’s fine to maintain your own opinions and beliefs, it is very unattractive to refuse to hear about others. A woman wants to be with someone who knows to talk and talk well.

Your date may be more concerned with how well you can tell a story than whether your clothing is on point.

9. How much you drink

Having a drink or two, at dinner or over a conversation is fine, but if you do not have the self-control to stop at a few, then just don’t drink.

Moderation is the key, women would sometime look for signs of dependency or the lack of confidence that requires alcohol to oil the wheels of conversation.

This is a sign that the man has not got his act together, a complete turn off to anyone that is looking for a long-term relationship.

10. Do offer to Pay

Although in 2018, men and women both have equal standing in every situation, it is important to respect this of each other. A tactful way is to offer to pay, and if she insists to split the bill, then split the bill and at least leave a tip. These little gestures will carry a long way.

11. Follow Up

Now your date was fantastic and you are confident there is going to be another date and you are so happy that you can’t wait to see her again. If you feel like sending a casual text later that night or the night after go for it.

One note is just don’t stalk her, resist the urge to scroll through her Facebook or Instagram pages and accidentally like their Instagram picture or even worse, their ex’s Instagram pics. A follow up is important, it shows to her that you are interested.

Here are some great discussions from women on dating, researched from the web

“You can tell a lot about a guy by the first date conversation. I like it when he takes the initiative to move the conversation forward. I mean, I interview people for a living so it’s nice when there’s a back and forth.”

– Dyan, 28

“I expect the guy to wear something nice, smell nice, plan something for the day, and pay for the bill (just for the first date, put down your torches!). But it doesn’t have to be in an expensive restaurant or a carefully detailed day trip. At the end of the day, what matters is that we both find out if we click and could go on a second date. I’ll really appreciate it if he would just take the effort to prepare and be a little nervous for the day, just like I think I would and be.”

– Katy, 22

“In principle kasi, ang expectation dapat is just to enjoy the company of your date and to know more about him. Pero siyempre, sa first date, ang daming expectations. Para kang nasa job interview!”

– Nina, 31

“First date? I expect him to pick me up at home, take me to a really nice restaurant, aaaaaaand foot the bill. I know it’s a bit sexist, pero I’m old-fashioned that way. Haha!”

-Alysse, 26

“Besides seeing how a guy would clean up and prepare for our first date, I look forward to really knowing his character. That’s why rather than simply seeing a movie and having dinner, I prefer something more adventurous to see how he would react to certain situations.”

-Sharlene, 22

“This might be an unpopular opinion, but as much as possible, I don’t want a guy to try hard to put his best foot forward on the first date that it makes him look like he’s already faking his character. I want to feel the authenticity of his personality as I get to know him. As cliche as this may sound, I just want him to be himself.”

-Jeng, 21

“I’m not big on dates, but when I do go out, I actually look forward to conversations. May it be over dinner discussing the movie we’ve just watched or over a cup of coffee talking about how our day was. So I guess I expect the guy to be comfortable enough with his own thoughts and wouldn’t mind throwing some of his ideas my way. Oh, plenty of eye contact and a good night kiss wouldn’t hurt too, especially if even before finishing off your coffee, you already know there’s going to be date #2.”

-Joys, 30

“First dates are always fun and full of surprises. I especially love it when my date can carry a good conversation. It’s also a plus if he’s spontaneous and game with anything.”

-Prei, 22

“Three things: communication, eye contact, surprise. First dates can be super awkward but if our conversation becomes comfortable and casual before the date ends, I’ll take it as a sign that we’ve hit it off. Eye contact is a huge factor, too-a good sign that he’s interested, or respectful at the very least. Dinner on a first date is typical but plus pogi points if he can come up with something unique and unexpected.”

-Joy, 28

“I think getting to know the guy more is what I really look forward to in a first date. I’d like to observe and know how he is as a person. Does he treat the waiters well? Does he throw his trash in the proper area? Is he caring about his family? Little things like that already show if we’ll get along, or if we share the same values. I don’t mind if the first date is somewhere fancy or kahit sa mall lang.”

-Trina, 23

“When I’m going on a first date with a guy, I usually just hope that we get along and that he has something fun planned. ‘Yung more than just the usual movie and/or dinner at a restaurant setup. And I expect him to be well-mannered and dressed appropriately.”

-Ramona, 3


Alright, you have opened your wardrobe and you have nothing to wear that you feel will bring out your best first impression.  If you are about to go on a date or have decided to take dating seriously it is important that you are prepared.

Luckily there is help out there for these sorts of things, personal stylist and image consultants are a great place to start. We help choose the best outfit for men, want to make a great first impression? Give us a call


At Winslow, our Outfit Designers have worked with several men, getting ready for their first interview or going on a first date. If this is something you need help, reach out to the professionals and we will help you deliver a good first impression.

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Ashan Winslow

Ashan Winslow, the man behind Winslow Style – knows what it takes to be a leader in the menswear style industry. His passion is to create bespoke and made to measure menswear clothing be it an event to attend or refreshing your closet.

He is an experienced image consultant in Sydney to provide a personalised one to one service at the convenience of your office or home. Winslow Style works with customers from all walks of life, from the power real estate broker and the corporate executive to the entrepreneur looking for a new look or the groom who wants to attend his wedding in a perfectly tailored suit.

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