The best way to approach a woman

Approaching a Woman

There is no magical formula or trick in how to approach a woman and successfully start a conversation. However, pick up lines do not work. Repeat, pick up lines do not work. Having bartended for many years, too often I have seen the awkard silence, bored look, or forced smile in the aftermath of a failed pick up line. So what to do then? I will give some general rules about what to say when you approach a woman, where to approach her, and how to determine who to approach.

Who to Approach

Generally, within less than five seconds a person can tell if they have an interest in or attraction to someone they first see. This is typically based on physical appearance or something that they can observe. However, do not think that based on this that you are either doomed or that you have a sure thing because what you say or do after that initial impression can either help or harm your cause tremendously. So why do I mention this? What does this have to do with approaching a woman? Its simple, approach women that look approachable. What makes a woman approachable? There are a few things.

  • Body language- This is one of those things where you develop a "feel" for over time. Some that I have observed is if a woman starts to groom themselves, like straigtening their clothes or hair, it is generally a good sign. Repeated glances or a prolonged look is also usually good news. There are many signals that you can get from observing a woman's actions. So don't just rush in take your time see if this is someone that might be interested in being approached. Also, there are many sites that provide tons of information on this subject if you are still unsure as to what to look for.
  • Who they are with- I have found it is easier to approach women that are alone or with a friend, preferably a female friend. So if there is a group of 12 women for a bachlorette or birthday party, I would recommend passing as you are basically approaching the whole group of women, which is much tougher. If a woman is out with a male you might want to pass. Sure he could be her brother, but its more likely it is someone she is in a relationship with or pursuing a relationship with. Things can get ugly if you hit on someone's wife. However, if you are willing to take the risk because you are just completely smitten then at least do yourself a favor and watch their interactions for awhile, it might save you on some hospital bills or from having to post bail. If a woman is out somewhere with her children I recommend passing. This is more of a personal choice but typically, and this is especially true in regards to small children, when a woman is out with her children she is not looking to meet someone. Now depending on the place or facts surrounding the encounter the last statement may not be true, but as a general rule I usually pass.

What to Say

So once you have found someone that seems approachable what do you do? Again there are no magical words that work every time. So much depends on the situation, the person you are approaching, and the place. But there are some general guidelines you can follow that should help. Like many things in life it is not only what you say and do but also what you don't say or do that can influence the ultimate outcome.


  • Keep it light- This doesn't mean you have to talk about the weather but it also means you shouldn't confess your deepest darkest secrets the first time you speak to someone.
  • Stay Positive- Don't be a Debbie Downer, so make a positive comment or remark.
  • Respect personal space- If you get too close it often makes others uncomfortable and making a woman uncomfortable would be very counter productive. Also, when walking up do so slowly do not "rush" her. This will also tend to make her uncomfortable.
  • Humor- Say something funny. Laughter tends to put people at ease. This doesn't mean telling knock knock jokes. A funny observation of the curent situation often works best. Also keep it short. Witty is fine but don't overthink it to the point to were it seems forced or unnatural.
  • Confidence- This is often the hardest part because approaching a stranger for the first time can cause some anxiety or nervousness. If you stammer about or seems anxious or nervous it can make a woman uncomfortable. Be at ease, take a deep breath before approaching. Don't talk too fast, too loud, or say "um" ten times. Use a conversational tone and try to project ease with the situation. However, there is a difference between confidence and cockiness, so be confident not cocky.


  • Hard Sell- My friends and I also call it the full court press. Basically don't come on too strong. The skill lies in not making it apparent that you are "picking her up" or "hitting on her", rather you are just starting a conversation. Put her at ease not on edge.
  • Try to Hard-Desperation is sad and it is easy for someone to sense it. This ties into the hard sell as well. If it becomes apparent that she is not into you or the conversation, then simply thank her for her time and move on.
  • Be "Dramatic"-  Be yourself. Do not attempt to be mysterious, sultry, or anything else you normally are not. People, especially women tend to see through any facades. When approaching someone and introducing yourself, do not sell someone you are not, be your natural self.

Not a Good Sign

Where to Approach Women?

Everyone might have a different circle of places they go. Some may go to bars, but not the gym, and so on. So I will list places or situations where women might be more likely to be approachable than others.

  • Work- Typically a bad idea to attempt to "meet" someone at your own place of employment. Also, trying to meet someone at their place of business can be hard and often is not appreciated. So stop hitting on bartenders, waitresses, and sales clerks. Trust me on this one, when your not around they talk about how sad it is. They feel trapped into listening to your advances and most people do not like being trapped.
  • Gym- I know of people who have met someone at the gym. However, I don't like approaching people at the gym because most are there to workout not talk. Now if your getting a sense that someone might be approachable then go ahead, but I prefer not too.
  • Bar/Club- Go for it. Follow the rules above and you should be fine.
  • Grocery Stores/ Coffee Shops/ Bookstores etc.- I have had mixed results in shops as those listed.  As you become more confident and familiar with the process you should develop a feel of when is a good time to approach someone in this type of setting.


This piece is not intended to imply or say that women are such a foreign and alien creature to men that they need a guide book in order to approach them. Rather it was intended to help correct mistakes that I see repeated time and time again. Men, be yourself, be confident, and be respectful, just have a conversation and you will do fine.

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