The Sex Files with Emily Morse

How to approach Women (or Men!)

a man flirts with a woman at a barDear Emily,

How do I approach women? Growing up in SF during the seventies was not great for a man’s sense of masculine self, hearing what “pigs” men are. I choke all the time, even when I know a woman is into me…It’s like the Clockwork Orange treatment.



Dear George,

Approach someone even if you’re about to pee your pants you’re so nervous. Many men lament that they never get with women, but they never try to initiate conversations with them. It’s easier for men to make excuses like “women think all men are pigs,” than it is to put themselves out there and be proactive about getting dates. Instead of living in fear, join a hobby or group activity where interaction with new people is expected. If you want to avoid being perceived as a pig, practice using shrewd observations instead of lewd compliments when talking to women.

Here’s an example:

Shrewd Observation: “I like your dress, it looks vintage.”

Lewd complement: “Your ass is looking fine in that dress”

You have a much better chance of starting an actual conversation if you’re specific and show interest in her as a person, and not just as an object of desire. Even if you don’t immediately comment on her physical appearance, if you use generic conversation starters she’ll assume you’re only talking to her because you want to get laid.

If you can’t be unique, at least try to be relevant.

I know that it can be incredibly nerve-racking and tricky to approach women. She’s not always going to be wearing a T-shirt with your favorite band on it to easily facilitate conversation. But if you can’t be unique, at least try to be relevant. Ask her opinion on something happening in the venue. If a somewhat familiar song starts playing on the radio, ask if she knows who the artist is. Ask her questions and really listen to what she has to say. Then respond just as if you’re talking to a friend. If she gives you short answers and is avoiding eye contact, respectfully end the conversation and introduce yourself to someone else. If things are going well, try to keep the conversation going as long as possible before asking her out. Tell her you’d love to continue talking to her, would she like to grab coffee sometime? It’s that simple.

Remember, the worst thing that can happen when you approach women is you get rejected. Pick up the pieces of your broken heart, and try again. You’re not receiving a Clockwork Orange treatment, you’re just asking a woman to coffee. You can recover from rejection and try again with someone else. Unlike Anthony Burgess’s fictional character Alex, you have the free will to walk over to the woman at the coffee shop and say, “Hi. I couldn’t help but notice that you’re reading “A Clockwork Orange.” I love that book.”  Smile and see what happens. You’ll never know if you don’t put yourself out there.

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