As an entrepreneur and designer, I do a lot of user research.
The reason is simple: inside the business, we tell ourselves a story about our customers and the way our product and brand interact with the world.
Conducting user research is about figuring out which assumptions are right and which ones are wrong. It’s also about learning new things that you never even considered.
The goal is simply to get your story closer to reality.
I love this process of asking real people real questions and observing them in real situations. Recently, I decided to apply it to an area of my private life — an area in which I have never been particularly skilled, and where many others are struggling as well.
I wanted answers to everything I fear about approaching women.
For many single guys, walking up to a woman is one of the scariest things in the world.
It’s like laying your torso bare before the cold dagger that is mother nature. Will you be chosen or stabbed in the heart?
(Ladies, you know you’re in charge, right?)
Sure, there are some real casanovas out there. And some people are really good at social interaction in general. You probably know someone like this. But the reality is that most guys are not — and that doesn’t mean they can’t be a great person in all the other ways.
In theory, if you approach women enough times you eventually learn a thing or two about what works and what doesn’t. And there are those who call themselves “pick up artists” who basically do this for a living (granted, their motives often seem kind of questionable).
I am a little obsessed with doing things that make me uncomfortable, so I have done my fair share of approaches. But I have found that learning this way is inefficient and obviously demanding for most guys. As a result, many of us just don’t do it.
And in a world where Tinder is the new normal, it can even seem weird to talk to someone in the real world.
Because most women want to meet great guys as well. And it’s not always sufficient to rely on meeting someone from your existing social circles.
There are so many missed connections between good people.
To remedy this, I wanted to get some real answers from the “opposing team”, and help make the process of approaching someone smoother, more enjoyable, and more successful for both sides.
I am not saying it will ever be easy to approach someone. The harsh reality is that she may not be into you. That’s just the way it is.
Luckily, we are perfectly capable of ignoring this fact 99% of the time.
And yes, sometimes women approach men as well. But that is less common and also less stigmatic.
Lastly, it goes without saying there is a lot of nuance to the “rules” I have come up with here. They will never replace a set of good social skills and common sense.
I got together with my guy friends for some real talk over a glass of wine. What is the deal with talking to women? What is hard about it? What has seemed to work and what hasn’t?
I then created this Google form and sent it out to single women, some of whom are writers here on Medium and some who are part of my own social circle.
I even went on Tinder to recruit a number of “subjects” (yeah, I’m weird like that).
Many of the women I talked to had an emotional reaction and frustration around the subject (in user research, strong emotional reactions are the number one thing to look for — they indicate that you are on to something important).
When I had received all these answers, I was happy but eventually decided it wasn’t enough. So I posted the form on Reddit and received hundreds of answers in a matter of hours. Then they took the post down. But I ended up with 682 answers in total.
The women’s ages ranged from 16–50 and averaged around 23 years.
Roughly 80 percent of them were single and heterosexual (which is the focus of this project).
(Note: Like an idiot, I forgot to add a question about which country they were from. But I know some of the answers came from Swedish and American women that I personally recruited. And considering Reddit’s demographic it was probably a lot of Americans and then the rest scattered around the world.)
So without further ado, this is what I learned about approaching women.
Set and Setting
Set and setting are hugely important when approaching someone you don’t know. Often, a woman will fail to show interest in you, not because of you, but because it was the wrong time and place.
The best situations are the ones dedicated to social interaction.
- Coffee shops
- Bars/clubs (almost unanimous answer)
Optimally, the woman is with 1–2 friends (which makes her feel safer than if alone — more on this later).
Of course, this shifts the risk of embarrassment more towards the guy. But that’s only fair since he is the one initiating the conversation.
A little more nuanced
- Direct messages on social apps (this is mostly fine, and very low cost for both parties)
- At the grocery store
- In the park
- At a museum
- At a concert
- After class
If they are alone, it’s only OK to approach in settings with lots of people around and lots of space.
If they are with a large group of friends, it can be OK to approach but there is more risk of embarrassment and interruption for both parties. Usually, it’s better if the guy is also with a group of friends.
- At the gym
- Walking down the street
- On the bus/train or waiting for the bus/train (this is because they can feel trapped)
- Basically, any situation where the woman can’t easily extract themselves from the situation
- When they are busy / have headphones on / sitting with their laptop (UNLESS there are clear green lights — see Signs of interest below)
- Alone when it’s dark
* * *
Signs of Interest
Most women prefer to be approached by the guy, but there is a significant number of women who prefer to be the one to approach.
A good rule of thumb is to show your interest by paying attention to her (don’t be a creep) and then either wait for the green light (see below) or wait for her to come up to you.
The green light
In the comments on Reddit, someone told a story about how a couple of hundred years ago, women would drop their handkerchief but make it look accidental, so a guy would see the chance to have his sense of hero urge fulfilled and be like; “oh my gosh this chick needs her handkerchief — and I can help her!”
Then voila, conversation.
There are equivalents today. Not too long ago, a woman who later asked me out came up to me and wanted me to watch her things while she stepped out to meet a friend. This is a great and casual way to connect, and I think it can work the other way around too.
However, there is a more universal sign of interest:
The green light = repeated eye contact and smiling
Finally, something so straightforward even us dummies can understand.
Almost unanimously, if they are interested, women will make repeated eye contact with you and smile a lot (pay attention, it might be more like glances).
“If I see a guy I’m attracted to, I’ll often glance his way and smile or laugh. If we accidentally make eye contact I won’t look away as quickly.”
“Eye contact, I make it clear that I’m checking him out. Usually 2–3 times”
“Eye contact. Often I am too shy to even smile and will look away immediately but if you see me look at you repeatedly I am interested 99% of the time.”
Other signs of interest
- They will probably stay in your vicinity and in your line of sight.
- In a group setting, they might appear to focus solely on you.
- If she is with a friend, she will probably make a comment about you and they will maybe laugh a little.
- Basically, they will look interested (who would have thought, right??)
* * *
Making the Approach
This is the moment. You have established that you are in an appropriate setting. You’re pretty sure you’ve picked up on the green light. You’re good to go.
So, what are some important things to know as you make the approach?.
Make her feel safe
There is one thing that underlies everything else. And if you are a decent guy, it’s probably not that obvious to you. For me, it certainly wasn’t.
That thing is safety.
Let me state the obvious: women, on average, are smaller than men.
This means that women run a much higher risk of being physically harmed by a man than the other way around.
It’s not surprising then, that this turns out to play a major role when a man approaches a woman.
The number one rule of approaching women is to make sure she feels safe at all times.
- Don’t corner her — allow for plenty of room.
- Pay attention to, and respect her boundaries at all times
- Don’t try to force conversation
Be careful with commenting on her looks
There is generally nothing wrong with a genuine compliment. It is important to be attracted to each other and it’s often the reason we want to approach someone in the first place. But women are used to their attractiveness being the center of our attention. It doesn’t mean as much to them as it does to us. Therefore, it’s much more important to notice and appreciate something about her personality.
The easiest way to do that is to comment on something she consciously chose, like the shoes she is wearing or the type of coffee she ordered.
Lastly, if you go to a sexual place right away you run a huge risk of putting her off. This is often what typical players do. Have some class.
“Vague complements about my appearance can be creepy, but everyone likes a compliment about their outfit.”
“Just a note, compliments on my looks are nice and all, but if that’s all a guy seems interested in I’m instantly turned off.”
Make it light and fun, and don’t start flirting right away
This is similar to sexual remarks; if you start flirting right away you risk coming off too strong, not as someone who is genuinely interested in her personality.
When you approach someone, you are a salesman — you are selling yourself (actually, you always are when meeting new people).
No one wants to make a big commitment right away without knowing what they are getting into.
But everyone wants to laugh.
So, keep it light and fun and just see where it goes.
“Opening with a joke or a shameless line can work on me. To be honest the only thing that will immediately put me off is an explicit sexual remark.”
“I like it if he just makes a joke about something thats just happening in a more casual approach, not flirting right of the bat. Than you can talk without feeling that pressure that he wants something from me. Its much more relaxing that way.”
“Any casual conversation, like with a new friend you’re trying to make. As chill as the first day of classes, for example.”
Although it is important not to come off too strong, it is also important not to leave the conversation with ambiguity. After all, your intention is to get to know her and see if your interest in her can turn into something more. So, don’t be afraid to make your intentions clear. There shouldn’t be any doubt in her mind after the interaction.
“The important thing is to be intentional, if you’re interested, it’s totally fine to use a harmless excuse or compliment to start the conversation, but I really appreciate it when a guy doesn’t leave me wondering or confused what the interaction was.”
Be genuine and specific
Many women have experienced harassment like cat-calling or offensive attempts from disingenuous men. This naturally makes some women a little wary of men who approach them.
So, if you really are sincere, one of the most important things you can do is to be and show your genuine self. This is also fundamental for testing your compatibility. It doesn’t really help either one of you if she’s attracted to you when you are not being you.
Be completely honest about why you want to talk to this woman. What is it about her? BE SPECIFIC.
Don’t say “you have beautiful eyes”. That’s cheesy.
Instead, be honest and specific about it — what exactly is it with HER eyes that you find beautiful?
Now, that is still cheesy, we all know that.
But it’s much more genuine, and little details like that will make all the difference.
You don’t need fancy lines or generic flattery. Being an overly confident “smooth talker” (like you might picture guys who are “good with women”) can actually hurt you when approaching someone you are interested in.
Don’t believe me? There were many comments like this:
“Usually players don’t find it awkward to talk to you, whereas those who genuinely find you attractive and want to date you will stumble over their words or stutter or apologise a lot.”
“Players tend to have a lot of smooth, overused lines and act like they’re too cool for it. Genuine guys tend to be a little more nervous and honest.”
Note: Of course, being genuine is equally important if you are in fact just after sex. This is not the focus of this article, but there are plenty of women who are open to that kind of thing too. The only thing women generally have a problem with, which extends to all well-adjusted people regardless of gender, is when someone is being deceptive and not upfront about their intentions!
* * *
How to Know If She’s Into You
Now that we have learned some things about how to best make the approach, we also need to talk about how to interpret the results.
If a woman is into you, in general, she will not be subtle about it (if you know what to look for).
She will be engaged and invested in the conversation
- While talking, she will continue making eye contact and will try to keep the conversation going.
- She will be enthusiastic and ask you questions.
- She will pay close attention to what you are saying and will be engaged in your responses.
“I will usually ask them questions about themselves as well to show that I am also interested. Otherwise, I would keep my answers as short as possible in an attempt to try to end the conversation.”
Her body language will change
She will be relaxed and have open body language. Again, this tells you that she feels safe.
“My body language changes, I become more open to the person I’m interested in to show that they are welcome within my personal bubble, I am much more talkative and expressive”
“I smile genuinely, turn my body towards him, interestedly listen to what he has to say, and ask him questions that open a conversation.”
She might be touching you
If she is subtly physical with you, like touching your arm, this is also a good sign.
“My body language — I am a bit touchier with guys I’m interested in romantically. I might touch them when I’m making a joke or laughing or something. I also lean in a lot more.”
She might tell you
Some women will tell you outright that they are interested (but don’t count on it). They might do this by proactively giving you their number or suggesting to dance or grab a drink later.
“I’ll keep the conversation going, might even offer my number first before they (hopefully) ask for it. It depends on how things go.”
“I say, ‘I’m interested in you! Would you like to continue this conversation?’ ”
* * *
How to Know If She Is Not Into You
Even if you think you picked up on the green light discussed earlier, there is no guarantee that she is actually interested. You might have been mistaken or, after talking to you, she might have realized you are not what she’s looking for.
Pay attention to the small cues
It’s easy to be obvious when the feeling is mutual. Rejection is much harder. Most people don’t want to hurt other people. So, when they are not into you, most women will act disinterested and hope you can take a hint.
These hints are the opposites of what we discussed earlier:
- She will be tense and her body language will be closed off.
- She will only give you short disinterested answers.
- She won’t make an effort to continue the conversation or make eye contact.
“I will do literally anything other than directly telling them I’m not interested unless nothing else works.”
“Not making eye contact. Paying more attention to the people I’m with (or something I’m doing). Again, men cannot expect women to be upfront and blunt about their interest because sometimes that can result in a dangerous situation for the woman. Be vigilant for these cues!!”
She will make an excuse
If you cannot pick up on these hints, she might tell you she has a boyfriend or come up with some other excuse.
Basically, any conscious effort that makes it less likely for you to meet again or continue the conversation, is a clear sign.
This is the exact strategy of one respondent:
“First, I try to act disinterested. Next, make up an excuse. Then, tell them I’m in a relationship. If they still don’t give up, I tell them straight up to leave me alone”
At this point, my noble romantic knight, you are long overdue to politely wish her well and get the hell out of her face.
She might tell you straight up
Don’t count on this either. It’s uncomfortable and can be frightening. This response sums it up pretty well:
“We are scared of being insulted or attacked if we turn down a man’s advances so depending on the situation (alone/with friends), if the dude is 7 feet tall and 200 lbs we will choose different reasons. Obviously I would like to live in a world where I can just turn them down politely (and sometimes I have done so) but it is a genuine risk”
One more tip
This is another reason why it’s so important to be intentional and to make sure your “pitch” gets through. If you are not clear — she cannot respond clearly!
“It depends how clear they are. If they aren’t clear that they want to date me, I don’t want to be presumptuous and drop really obvious hints. If they ask outright, I’ll say something genuine about why I like them, but that I’m not interested in them in that way/don’t feel the same.”
* * *
Conclusion: The Irony of It All
The last question on the survey gave the women a hypothetical chance to send a message to every guy who would be interested in approaching them. The answers made something very clear:
The feeling is in large part mutual.
Obviously, women like meeting guys who approach them in a respectful way.
The problems that occur all go back to the physical dynamic between men and women. Any type of force used by the man, like not being able to take a hint or being persistent in his approach, is a symbolic transgression of this physical dynamic. As long as women feel safe and trust — it’s all groovy baby!
If I could draw one big unifying conclusion:
It’s never a problem to approach someone you are genuinely interested in. Nothing bad will happen. And you don’t have to be superman or woo her straight away. Just keep it casual. But it does not matter what you want if she is not interested. If she doesn’t make it obvious that she wants you there, leave her alone.
Finally, we must not forget the beautifully hurtful truth I mentioned at the beginning:
She might not be into you. And that’s totally OK.
Ironically, this is exactly the mindset you need to cultivate as a man. You see, there is such a thing as wanting something too much.
This is the number one rule of negotiating: the one who cares least about the outcome always wins.
If you approach someone while being overly attached to the outcome, not only does it put you in a vulnerable position — it’s unattractive too!
Of course, it’s a good thing that you really want the person. Your future partner will appreciate the fact that she was the one you were crazy about. But you need to find a way to hold that desire lightly and let it go as soon as life tells you that you were mistaken and it wasn’t meant to be.
I’d like to close with a lovely quote from Kevin Kelly, the former executive editor of Wired magazine, in his 68 bits of advice from 68 years of living:
Everyone is shy. Other people are waiting for you to introduce yourself to them, they are waiting for you to send them an email, they are waiting for you to ask them on a date. Go ahead.
— Kevin Kelly
* * *
I loved doing this project and actually learned a lot about women.
Did you think this article was accurate?
What do or don’t you agree with?
Feel free to leave a response and let us know what you think!
Thanks to Dan Moore.
Previously published on “Hello, Love”, a Medium publication.
If you believe in the work we are doing here at The Good Men Project and want to join our calls on a regular basis, please join us as a Premium Member, today.
All Premium Members get to view The Good Men Project with NO ADS.
Need more info? A complete list of benefits is here.