Having the Right Approach
Read her body language. Accurately reading a woman's body language can give you a good idea whether or not your approach is going to be successful. Most women make it pretty clear if they don't want to be approached by how they sit, what they have with them, how they react to you. Do not ignore these signs. Typically if a woman is reading a book, listening to music, or working intently at her computer she's not going welcome a conversational intrusion from you. Now, if she's spending a lot of her time looking around instead of working or reading she might be open to conversation. Someone whose arms are crossed across their chest and who is angled away from you (especially if they got into that position after making eye contact with you) is someone who doesn't want to be approached. Remember, that women are taught from a young age that they need to be pleasant to people and so, while she might verbally accept your intrusion into her space, her body language might be telling you differently.
Make eye contact. Eye contact is a fantastic and safe way to gauge someone's interest and openness to conversation. Try catching the eye of the woman you want to speak with. Three times tends to be a charm (as the saying goes). After the third meet of the eyes, approach her. A smile is also good for gauging interest. If she smiles at you, that's a pretty good sign she wouldn't be adverse to a conversation, especially if she does it without a first smile by you. This works pretty much anywhere. You can make eye contact at a crowded bar, a coffee shop, that bookstore you like, on a bus, on a plane.
Be confident in your approach. Confidence is one of the most attractive qualities in a person and a confident approach can get you further than a non-confident one. This doesn't mean that you expect the woman to delight in your company, but it does mean that her disinterest won't threaten your self esteem. You need to pay attention to your own body language: don't slouch and don't cross your arms across your chest (a defensive gesture). Have open body language, angle yourself towards her and don't fiddle with things or you'll appear nervous. Faking confidence is one of the best ways to trick yourself into feeling actually confident. So stand up straight and walk with purpose. Remember the worst thing she could do is not be interested in a conversation and that's simply not a huge deal. Her disinterest doesn't mean anything about you. So remind yourself of that.
Be yourself. This goes along with being confident. You need to remember that you yourself are a cool person and someone that people would enjoy talking to (as long as you're respectful). Don't be afraid of what she might think about you when you approach her. The woman should get a sense of who you are, even if it's a less intense version of you. So, for example, if you aren't into outdoorsy things don't pretend to be to impress her. She'll figure out pretty quickly that you're a phony and she won't be that interested. This doesn't mean that you should immediately whip out your Magic: The Gathering cards or hit her over the head with your MVP status on your college football team. It means that you have confidence in yourself and your interests. Remember, she might not share your interests and she might not be that interested in a conversation. Don't take her disinterest as a slight against who you are.
Use a respectful opening. The opening to a conversation with someone, especially a woman you would like to get to know better, can be really difficult and make you nervous. Never fear! There are some pretty good methods to get the conversational ball rolling. Ask for help. This could be something as simple as asking her which coffee shop she thinks is the best. If it doesn't seem like she's in a rush, ask her to join you for coffee at the place she recommended. Use your surroundings. If you're in a bookstore ask her if she knows where you might find a particular book. If you're both waiting for the bus, you could ask her the time and then make a joke how the bus is always late, especially when the weather's really bad. Ask questions. For example, if she's wearing something really cool, ask her about it. Say "Hey I couldn't help noticing you're wearing a Seahawks' sweatshirt. Are you a big fan?" or "Have you ever been to one of that band's shows? I hear they're amazing." It gives you something to connect over and opens the possibility for further conversation.
Talking With Her
Have a natural conversation. Once you've broken the ice, you'll want to have a natural conversation with her. This can grow naturally out of your icebreaker comment. For example, if she says that she's a big fan of the Seahawks, you might talk about them winning the Super Bowl and where you both were when that happened. A compliment is also a good thing to drop into your conversation so she knows you're interested in her. This shouldn't be something grandiose like "You're the most beautiful girl I've ever seen" (it comes off as insincere). Instead say something like "Your outfit really matches your eyes. It's a great color" or "Those earrings are amazing. Did you make them yourself?" For the bookstore example, when you've asked where a particular book is, ask her if she's read it. If she doesn't say that it's one of her favorites then ask her what her favorite book is (or favorite genre, since choosing a favorite book can be difficult). If you've offered to buy her a drink at a bar and she's accepted, you could talk about some of the funniest things you've seen intoxicated people do. This will make her laugh and allow her to reciprocate with funny stories of her own.
Listen to her. A woman will notice if you're spending the whole conversation staring at her breasts and not listening to a word she says. Likewise, she'll be very put off if you spend the entire time burbling on about yourself. When she speaks, listen to her and ask questions that show you're interested. Ask her opinion on a subject, even if it's something as basic as whether bluegrass is better than country music, or whether she thinks the education system is really screwed up. Don't fiddle with things, or check your phone, or start looking around the room while she's talking. Be really focused on her. Otherwise, she'll quickly notice your disinterest and respond with disinterest of her own. If you find your mind wandering while she's talking, or find that you aren't interested in what she has to say, tell her that it was nice to meet her and edge on out of the conversation.
Fascinate her. You want your conversation to get her interested and not be the same old boring "what's the weather like" routine. You will want to show her what makes you unique and why she would want to continue the conversation. Talk about something that you're really interested in. For instance, if you're on your way back from something cool (like you were just at a concert) mention it. If you taught yourself Japanese, work that into the conversation (you can even throw in some humor by mentioning how difficult it was and some of the hilarious screw-ups you had). Find something in common. A good way to set up some mutual fascination is to find things in common to talk about (like those Seahawks). If it seems like there is a bond between you, she'll be more likely to want to see again and continue the conversation. If you're at a bookstore, find some mutual books you both enjoy; if you're at a concert, chat about different kinds of music. Even things like laughing over a late bus can set up commonality between you two. Tell her something interesting. Show her that you're the sort of person who is interested in the world. If something has happened lately in your city or town, discuss it.
Demonstrate your sense of humor. Humor can create a bond faster than anything else. Of course, you have to remember that not everyone has the same sense of humor. Fortunately, there are some types of humor and things you can say that have a good guarantee for making the woman laugh. Gently poke fun at yourself. This will show that you don't take yourself too seriously. However, you want to make sure you aren't belittling yourself. Tell her about the time you got on the wrong bus and ended up halfway across town or when you gave your friend a big hug, only for it to turn out not to be your friend. You can also mention something really funny that you saw. Maybe you noticed a really short person get tangled up when they were walking a bunch of dogs, or you happened to witness a whole troupe of clowns exiting a bar. Real events tend to be more funny than just saying funny things and can lead to a mutual conversation as she recalls funny things she's seen.
Know when to back off. Sometimes it doesn't matter how funny or charming or nice you are. Not every woman is going to want to have a conversation with you. Remember, no one owes you time or energy and if she seems uninterested in the conversation, back off nicely. If she's only answering in monosyllables, or she keeps checking her phone, or not making eye contact, she's probably looking for a way out of the conversation. If she's with people who are rolling their eyes at the things you say or are trying to ignore you, again it's time to end the conversation. Show that you are a class act. Don't sarcastically say "Well, I can tell you're not interested in talking to me," or "Sorry to bother you." Instead, say pleasantly "Well, it was nice talking to you. See you around."
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