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Step 1
Remember the old business advice of, "Location, location, location." This also holds true when it comes to flirting with women. To hone your skills, frequent public places that aren't overrun with men or couples, and aren't deadline oriented. That old standby, the produce department, isn't a bad choice. Rarely do you see many men, and the atmosphere is fairly relaxed. Women like to take their time examining the vegetables, so put yourself out there right along with the peaches and avocados as something to consider. It takes time to find the right semi-ripeness of certain foods, while others, like potatoes, are tossed into the cart one bag at a time. In other words, loiter around the seasonal fruits. Other locations where you have time to scope out the scene without being rushed include long lines at the bank or post office. Don't do your banking at 11:00 a.m., when the only women in the bank are grandmothers and stay-at-home moms; hit the bank around 5:30, when the single, working gals are lined up. Choose the longest line. Finally, lunch hours are a good setting for finding potential flirt-mates, providing you aren't hanging around a place where lunch breaks are only 30 minutes. Find a park in a downtown location that is near a large office building, as these women likely have an hour lunch. Don't wear jogging attire; it could send a message that you are unemployed. Wear business casual clothing and show up just before lunchtime. Place yourself in a spot that allow for easy viewing of the main thoroughfare so you aren't having to crane your neck to see who is nearby.
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Step 2
Don't forget the props. Once you've got your location staked out, show up with the appropriate props. A newspaper (not the classifieds), beverage or easily edible snack provide both a comforting distraction in case things don't go well, and fodder for striking up a conversation. You also need a pencil or pen, and possibly a business card or other scrap of paper. Under no circumstances should these be easily accessible. Dig for them so as not to suggest you came fully prepared to meet someone. Now that you have the setting and the props, it's curtain time.
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Step 3
Be casual. For some men, this is about as easy as de-activating a live bomb. Take long, deep breaths and find a pleasing visual to focus on that can bring you back to the moment if your mind begins to wander into no-man's-land. Take the scenario of the park bench. You are sitting on one end of a bench, and a female is at the other end. Angle your body so that you are naturally looking in her direction, but just past her so that it isn't uncomfortable. This allows you to make eye contact in a natural way as you flip the pages of the paper. This is where you ever-so-briefly smile and then look back down at your paper. Wait a few minutes, but not too long, and do the same thing again, this time holding the glance just a split-second longer. Maintain contact with her eyes. If she does the same, speak up: "What a beautiful day" or "I can't believe this weather" are both easy and natural, but make sure you aren't exaggerating. If you get a smile and then she looks away, you may need to back off. But, if you get a verbal response that in any way adds to what you've just said, you're on the the next step, which is The Bearable Lightness of Being.
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Step 4
Stay calm and keep the conversation light. Do not talk politics. Do not talk about the mortgage crisis. This is the time for small talk. If there happen to be two women present, do not monopolize the conversation. Include both women if the conversation lasts more than 60 seconds. Make eye contact with both, even if just one is definitely catching your eye. Pay a bit more attention to the woman you are possibly interested in by directing the questions to her, but not only about her. Example: "Do you ladies work in the same office?"
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Step 5
Be flexible depending on the situation. The key to successful flirting is knowing your audience. A woman at a nightclub is going to be under pressure to spend time with her girlfriends, so position yourself in such a way that a particular gal has you in her line of vision. A quick smile if you make eye contact goes a long, long way at a bar, because there are probably many women you could smile at. Don't think that women don't realize that. If she smiles back, hold the glance a bit longer and then take a sip of your drink while you avert your eyes. Move around the bar, maybe quickly visit the restroom, but don't wait longer than 5 minutes to make eye contact again. This kind of flirting should be subtle; don't raise your glass from across the room and by no means should you ever wink. Winking is for game show hosts.
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Step 6
Continue flirting once you actually have a conversation going, especially if other people are involved. Perhaps you can catch her eye while you are both listening to one of your friends discuss his recent business deal. A quick smile says, "I'm listening to him, but I'm paying attention to you." It is a good sign if she smiles back. At the soonest possible break in the conversation (be sure not to interrupt--very bad manners!), pose a question to her. This type of flirting is much more direct and is noticed. You are sending her the message that you are more interested in her than the other people in your group. Ready to seal the flirting deal? Keep an eye on her drink; as it gets to be near the bottom, offer to buy her the next one. Don't use the word "buy," however. Instead, say something along the lines of, "I think I'll order another drink. What are you having?" A quick smile, regardless of what her answer is (it might be, "Oh, I'm done for the night, thanks), keeps the flirt vibe going.
