How To Approach Women On The Street

how to approach women on the street

How To Approach Women

For the average man, knowing how to approach women on the street doesn’t always come naturally– and if you are ugly or not-conventionally attractive, it can be a very daunting task.  Approaching beautiful women can be tricky business.

One misstep and you can come off as creepy, annoying, or just plain weird. It’d be so much easier if there were some magic formula or code to follow that could guarantee success. Fortunately, there are some tips that will help you talk to women you just meet, and possibly ask them out on a date.

Make Eye Contact

how to approach women on the street

When you see an attractive woman on the street that you’d like to talk to, the first thing you need to do is make eye contact. Not intense stares, mind you. Just a quick glance followed by a smile.  If she continues to hold your gaze, smiles back, or even waves, she’s most likely open to being approached. If she doesn’t smile back or if she looks away quickly, then it’s best to leave her alone. No sense in bothering someone who’s obviously not looking to chat.

Start with a Compliment

how to approach women on the street

Once you’ve made eye contact and gotten a positive response, it’s time to start the conversation by giving her a compliment. Giving a compliment is helpful so you have an excuse to talk to the woman you’re interested in, plus you can gauge how responsive she is to you. 

Typically, if she just replies with a thanks and keeps walking, she’s not looking to be approached. If she opens up a bit giving a bit more details on your compliment or gives you one back, she’s likely to be more open to chatting.

Be sincere and genuine in your compliments. Nobody likes disingenuous flattery. If you’re going to compliment a woman, make sure it’s something you actually mean and is specific to her. Women love feeling like they’re something special about them that you drew you in.

You can tell her you really like her hairstyle, eyes, makeup, shoes, or outfit. It may seem superficial but these are areas women tend to spend the most areas on so praise on their efforts would be appreciated. Don’t insinuate anything sexual. Keep it cute and wholesome. 

Related: How To Reject Someone Nicely

Ask an Open-Ended Question

how to approach women on the street

Assuming that everything is going swimmingly so far, it’s time to ask her a question. But not just any question will do; this question needs to be open-ended so that she can’t just give a one-word answer and walk away from the conversation.  “Where are you from?” or “What’s your major?” are both good examples of questions that fit this bill nicely.

Ask her a question that’s relevant to the task at hand. If you’re at the grocery store and see some strange product in her cart or on the shelf, ask what she’d use that for. If she’s wearing a shirt with a band logo, ask what her favorite song of theirs is.

Asking an open-ended question will give her a chance to respond more fully than she could with just a yes or no answer—giving you more opportunities to keep the conversation going and get to know her better (not to mention giving her more opportunities to size YOU up).  

Don’t Do A Drive-By

how to approach women on the street

Cold approaching a woman on the street and asking for her number right away will generally have a low chance of success. Many women are approached like this often and will just quickly decline with a ‘sorry, not interested’.

It’s best to at least initiate a few minutes of conversation before asking for her number or a date. Show her you have more interest in her than what initially attracted her to you, her looks. A drive-by may give off the impression that you just run around, collecting as many numbers as you can. 

Ask For Her Number Not Social Media

how to approach women on the street

When you do feel there’s enough of a spark to ask a woman you’ve just met out on a date, ask for her phone number. Many women report that it’s becoming more common for men to approach them and only offer a Facebook or Instagram handle.

While social media is a great way to get to know what someone is like, women find men who want to exchange phone numbers as being more serious. Likewise, if she only offers her social media, she’s also most likely not overly interested.

Related: What’s The Truth? Do Women Like Dad Bods?

Don’t Approach Women At Work

how to approach women on the street

It’s generally not a good idea to approach women while they are working. That may seem impossible since for some, the only time you interact with women is when they are working! If someone is on the clock, you can assume they are busy or may not be in the best of moods. 

Some women may also be more hesitant to give out their phone number if their co-workers are watching. It could leave them feeling embarrassed as if they’re desperate for taking a number from a customer, or they may want to avoid gossip.

It’s also important to remember, the pretty waitress who is talking to you and may even be flirting with you is doing so because she is being paid to. That’s not to say it can never happen, but don’t confuse good customer service with flirting.

Be Confident

how to approach women on the street

While it may seem obvious, being confident or timid can be the deal breaker. A smile is a great sign that someone is positive and comfortable with themselves. Speaking loudly and clearly (without yelling and in the proper environments) can also make you appear more confident.

Whatever you choose to say, be sure of what you want to say without stammering or rushing. If you misspeak or say something cringe, just stick with or laugh it off. 

Some women may find nervousness endearing, but a strong, confident man will attract more admirers, opposed to someone just talking to you out of pity. There’s no need to feel down about yourself if you are rejected. Even the most handsome, confident men hear a lot more ‘no’s’ than you’d think.

Take Rejection Gracefully

how to approach women on the street

If a woman declines your advances, take the rejection gracefully by wishing her a good day and continuing on with yours. There’s no need to try to convince or persuade her to change her mind. If she’s not interested, it’s time to find someone else who is. Many women tend to automatically decline dates when cold approached on the street. 

Some women may already be in a relationship or just aren’t interested in dating at the time. If you run into them in the future, it’s better they remember you as someone who’s cool and approachable.  And who knows, they may take into account that you were interested in the past and may even approach you. Worst case scenario, if a woman does not give you her number, offer her yours and hope for the best.

Related: See How To Style A Flannel With A Hoodie.

Be Yourself

how to approach women on the street

The most important step of all can also be the hardest: being yourself! You may find yourself saying things you normally wouldn’t say, especially when you’re nervous or feeling out of your element (like when talking to an attractive woman). We tend to try to emulate someone else or something we’ve seen in a movie when in challenging situations.

Women can tell when you’re not being genuine, which will come off as sneaky or deceptive. A disingenuous pick-up line or other pick-up tactic like ‘negging’ will easily be sniffed out and give off either insecure or player vibes. Plus, it will be difficult to keep up the charade, if you do happen to land yourself a date, with a different personality other than your own.

Related: How To Get A Deeper Voice

It’s best to be completely who you are (well, showcasing the best of who you are at first) to know if a woman will be interested in you. A little more bravado and charm may be needed but not to the point where it’d be uncomfortable to uphold on a normal basis. You will also be more confident if you are being your true self and nothing feels better than someone being interested in you for being you.


Figuring out how to approach women on the street, especially for unattractive or ugly men, may seem daunting but is not impossible.  A lot of what it has to do with is being confident, being true to yourself, and just not being an A-hole. Having a casual conversation with a stranger isn’t stressful, and talking to women should be approached the same way. 

Don’t put yourself under the pressure of putting someone on a pedestal and needing to do back-flips to win them over. Women are looking to make a connection just as much as you are. First introductions are the hardest, but if there’s a spark, the rest will come easy and naturally. 

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Spacey Chan

Hello! I'm Spacey, representing the Windy City. I've been a hairstylist and makeup artist for over a decade, transitioning from bustling salons and makeup counters to my own independent beauty consulting business. Fashion and design are my passions, from tracking runway trends to sharing makeup tips. In my downtime, you'll often find me hitting the gym or engaging in a high-energy cardio or spin class.

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