Breaking the ice – How to talk to a woman in any situation

Man and woman flirting at a Christmas gathering.

Want to know how to talk to a woman? Being by conversing like a human being. Worry about monkey love later. (Photo Credit: CC BY/Rolands Lakis/Flickr)

Is there a hidden secret to breaking the ice in the dating sphere? If you have self-confidence and a good sense of what constitutes sexual harassment, not really. So before you plunk down money for that dating self-help book, here’s how to talk to a woman without seeming like a creepy stalker with a Selena Gomez shrine in your parents’ basement. Make the obvious small adjustments yourself, depending upon your sexual preference.

How to talk to a woman – On the street

It all begins with paying attention to whether or not she wants to engage in conversation with you in the first place. If she is walking fast, focused on her phone and avoiding eye contact, don’t force your way into her bubble. Also, don’t bet all your chips on one-on-one street conversation after dark. Nobody owes you conversation. However, if you make eye contact and she gives you a small smile, that’s an invitation to say hello. Start with small talk and see where it goes. Try to work in a compliment that isn’t about something physical or sexual. Perhaps a colorful necklace? Could be a history there, which in turn could spark additional conversation!

How to talk to a woman – At a cafe

If she’s studying or on the phone, don’t be rude and force her to stop what she’s doing so she can talk to you. Without being presumptive, if you’ve passed the eye contact smile test, walk up and ask if the other seat is taken, and if not, would she mind if you joined her. If you are both regulars at the cafe, you have something built-in to talk about. But if your advance is rejected, don’t take it personally. Go enjoy your coffee at your own table.

How to talk to a woman – On public transportation

Women frequently have their guard up when riding public transportation, as some of the creepiest people alive are more than willing to infect fellow bus riders with their personalities. That means that flirting opportunities will be few and far between. The eye contact and smile test – and that’s brief eye contact, not an intense stare – is always the best initial test. If headphones, a smartphone or book are in play, hold back. The non-physical, non-sexual compliment is an option if you connect, but keep in mind that what works on the street may not work as well on the bus or trolley.

How to talk to a woman – Who is your waitress

Servers work for tips, so don’t immediately mistake hospitality and a smile for an invitation into her dating life. Sometimes, there may be a few flirting signs that make it through – a whole hard wink, discreet lip-licking, et al – and if such is the case, extend yourself a little. Don’t make her feel like her tip is dependent upon accepting a date with you. In fact, settle the bill early and linger for that last cup of coffee or water. Then, if things aren’t too busy in the restaurant and you can catch her eye, tell her you’d like to meet her for a non-threatening cup of coffee, and ask if she’d be interested. Assuming nothing, risk a little and if things don’t take off, don’t take it personally. Of course, if she writes her number on your receipt, the path is open. But that almost never happens.

How to talk to a woman – Next to you on a plane

If you’re on a long flight, making conversation can help pass the time. If there are no barriers to conversation such as books, headphones or computers, read her responses to your conversation. If there are smiles and laughs, you will not be out of bounds if you up the ante a little. Considering that you may be traveling to different cities, you may have to settle for some contact info. If it isn’t phone digits, at least try to get a social media handle.

The Wing Girls – How to tell if she likes you


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