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Opening Lines and Conversation Starters

Many men are bewildered about how to start a conversation with a woman because of inflated anticipation, which isn't fair to either of you.  She's human, and it's okay to initiate a conversation with her the same way you would with any other human being: "How are you today?" or "Good morning”.  But, you have to keep it going, keep it interesting, and keep her attention.

First Things First

The next time you go somewhere, get into the habit of saying: "Good morning" to as many people as possible.  Once you're comfortable with this, add the phrase: "How are you?”  This simple exercise sharpens social skills, and helps you become comfortable speaking to those you don't know.  If you don't talk to anyone, and just wait until you see "her", your social skills will be lackluster and uncomfortable.  You'll also be nervous and awkward because you'll have more invested in the interaction… so, practice!

Out of the Norm

Take the conversation out of the norm it started in, to avoid being relegated to the same bin as every other guy she’s talked to that day.  You need to keep the interaction moving and fun, or else you will find it coming to a halt.

  • The next time you see a guy approach a woman, fail and then walk off looking a little rejected, walk over to the woman, smile and jokingly ask, "Hey, how did that last guy go?"  This always gets a laugh, and also shows you realize that when most other guys approach, they are sleazy or say the wrong things.
  • “Hey, I know this is completely random, but I saw you across the $PLACE and I just really wanted to meet you, or I’d be kicking myself for the rest of the day.  I’m…”
  • “Hey, you looked like you might be cool, and I wanted to come over and meet you.  I’m…”
  • “You seem like you might be cool.  Are you friendly?”
  • Hell, I’ve had a female friend who would go up to anyone and make the joke – “How much does a polar bear weigh?”  You laugh, but it worked.  Or, how about: "Do you have any raisins?”  When you hear the response “no”, you say, “Okay, then how about a date?”  Chances are the woman will smile, which gives you a perfect opening.
  • Social questions like, “Do you know where the Starbucks is?” and “Do you know which subway line gets me to Tribeca?” are innocent, low-investment and offer low-risk.  The odds are good that the person you’re talking to will respond; HOWEVER, you need to follow up – otherwise, the conversation is simply going to end with an awkward “…well, thanks. G'bye.”  And you end up shuffling away, kicking yourself, and wondering what the hell went wrong.
  • The next time you see a woman in the vegetable section of a supermarket or in a green grocer, walk up, smile and jokingly ask, "So... what are you cooking me for dinner tonight?"  This shows a lot of confidence, and if you smile and ask in a joking way, women see it as charming.


Situational Openers

A situational opener is a conversation starter that is based on the situation around you.  Although that might sound obvious, many times guys don’t use one.  Quickly observe the surroundings, and find something you can ask her about that would ENGAGE her in conversation.  Simple, innocuous comments and small-talk about whatever the situation happens to be around you will do just fine.  Here are a few effective conversations starters:

  • Grocery store -- "Excuse me, which steak looks better to you?" or “How do you tell if the ___________ (melon, avocado) is ripe?"
  • Coffee shop -- "Have you had the ______?  I was thinking about getting it."  Most women are pretty good at talking, especially if there’s any interest on her part.
  • Laundromats -- "Would you like to go have a cup of coffee while we're waiting for our clothes?" or "Could you tell me if I should wash these clothes in cold, warm, or hot water?"
  • Bookstore -- Note the book's title and determine the type of book it is (romance novel, etc), and then ask her a question about the book.
  • Restaurants -- "This is my first time here. What's good on the menu?" or “Would you like to go have a drink after dinner?"  Another option is, if there is something the person is, or has, that truly intrigues you, simply use that as a conversation starter.  This could be as simple as admiring a piece of clothing, or asking them about the food they ordered.
  • Beaches -- "Would you like to play some ______ (volleyball, Frisbee, football)?" or "I'm going to the store.  Can I bring you back anything?"
  • Bars and clubs -- "Do you want to dance?"  If she says no, whatever you do, don't just walk away.  Follow up with, “If you don't want to dance, do you mind if I join you for some conversation?"  If you are standing next to someone you want to strike-up a conversation with, comment on an item that you both share in your immediate surroundings, such as the long line you’re both waiting in, or the wobbly chair next to you.  By focusing on something you’re both experiencing, you’re eliminating any potential awkwardness from a canned comment.  If the nightclub has live music, ask her, "What do you think of the band?"


Remember KISS - Keep It Simple Stupid

Keep in mind that starting the conversation, and keeping the conversation going, should be unique and memorable, but also simple.  Typically, the open answer or question works best; drawing the woman to you out of inquisitiveness.  You can be playful and funny, but it needs to be presented with confidence and a huge smile.

  • “Hello” -- A simple “Hello” is the best conversation starter.  Certainly, you will need to be prepared to carry the conversation further, but at least you will have an opportunity to do so.  A quick, “How are you today?” works, too, for a straightforward follow up.
  • A Look -- Sometimes a look is all that’s needed to break the ice.  When faced with a person you find attractive, why not give them a genuine, 3 second smile?  You may be surprised when the object of your interest starts a conversation with you, instead!
  • “Good-bye” -- If you are going to see the woman again the next day (you work together, or attend the same school), you can break the ice by saying goodbye to the person you are interested.  After saying "good-bye", quickly follow up with a quick introduction, or something like “Have a good evening”.  From there, the ice is broken; making it easier to open a conversation the next day, or in the future.
  • “I couldn’t help but notice you” -- A nice compliment can be a great opening line, as long as the compliment is not followed by a cheesy pick-up line.  Follow the statement with something like, “Seriously, you’re very pretty.” or “You just have such gorgeous ________ (eyes, hair).”  Be honest and sincere.
  • “May I buy you a drink?” -- If you are in a bar or club, offering to buy a drink is acceptable.  If she says yes, then you can continue by introducing yourself.  If she declines, just politely bow out with “okay” or proceed with conversation.


I hope these suggestions have given you some ideas on how to approach a woman you’d like to meet.  Play around with the lines, and come up with openers you’re comfortable with.  Being prepared will eliminate the awkwardness, and she’ll be impressed with your confidence and composure.  Good luck!

by Aaron Marino

Past Topics

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Smoke and Mirrors | Short Men’s Fashion -
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Hello!  My name is Aaron Marino and I’m five feet-six inches tall.  If you’re one of the millions classified as short, I understand the wardrobe challenges we have.  Dressing can be especially frustrating and disappointing – from finding the right clothing to wearing it properly –  so, I’d like to share what I call the “smoke and mirrors” way of dressing to look taller. This artiRead More»
Out the Door Checklist | Preparing for a Date -
December 14, 2011
So, you are going out on the town.  It may be a hot date you have been working towards for months, or it may be your wedding anniversary, and you are surprising your wife with a well planned night on the town.  This night is special for more than just one reason. You took extra time and care while picking out what to wear. You put on a bit more deodorant (not your typical single swipe applicatioRead More»
Image Killers | Men's Style Details -
December 14, 2011
Ever wonder why it takes your wife so long to get ready?  Does it blow your mind how she tries on six different outfits before she decides on the one she will wear?  Well, gentlemen, the answer to these age old questions are… because she is paying attention to minor details that she knows make a difference. Before she leaves the house she makes sure that all pieces of the image puzzle are in oRead More»
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