A quick guide to not being creepy or weird.
I recently wrote an article about a man who walked up to a nice-looking woman in a restaurant and got shot down like a stunt plane in Top Gun. There were comments. So. Many. Comments. There was one that popped up a number of times that warrants some discussion, one question that I have been mulling over for days now.
“Well, how are men supposed to meet women and talk to them these days?”
I truly love the idea of meeting people organically. Humans are inherently social people. Opportunities to meet others endlessly present themselves. This just requires some finesse and understanding of social cues. This is where I see men fall flat on their faces.
It doesn’t have to be that way. Sadly, I think this may be a result of men receiving horrible advice from other men on how to approach women and win them over. If you want to see a horrific, yet humorous example of this, watch Ryan Gosling coach Steve Carrell in Crazy, Stupid Love. So much cringing.
The reason men get brushed off, or worse, when approaching women stems from one thing: men rarely take a moment to understand what it’s like to navigate the world as a woman. They don’t understand how we perceive them, their words, and their actions.
Once men do this, they create an environment where the approach is not an act of aggression but rather a social interaction based on respect. Respect is sexy.
My goal is not to run down a list of everything men are doing wrong. No man needs that beat down. My intention is to offer suggestions based on the feelings of your target audience. Remember that we judge ourselves on our intentions and others judge us on their perception. These two things need alignment.
Know how to start a conversation
Pick-up lines never work. Ever. Not even when you use them ironically and you think you’re being cute. The crash and burn I mentioned earlier started with this line: “My dog has been staring at you from across the room for an hour and you’ve not even noticed.” This was said as the woman looked down and saw that the dog was licking himself. Fail.
Starting a conversation with a woman has to be done in a non-threatening manner that opens a door to communication. Please, do not lead with a physical compliment. I know it sounds like it would work, right? It doesn’t.
Emphasizing a woman’s physical attributes often makes them feel uncomfortable. It’s creepy. That doesn’t mean you can’t give a woman a compliment.
Here’s the difference:
Bad: That dress looks hot on you!
Good: That color looks great on you!
See the difference? One focuses on the physical shape of the person in the article of clothing. The other focuses on the actual article of clothing. There are a lot of things to compliment a woman on that do not make her feel objectified. Trust me.
Telling a woman wearing big, bold earrings that she’s rocking them calls attention to you noticing her style and uniqueness. She spent some time picking out those earrings. I see your hamster wheel spinning. No, we will not think you’re gay. We’ll think you’re paying attention to details.
Never underestimate the power of a wingman
There’s nothing wrong with starting a conversation with a woman if both of you are by yourself. We often find ourselves in the same place at the same time as someone else, like standing in line at a grocery store.
But, sometimes there is strength in numbers. Two guys striking up a conversation with a woman they’re sitting next to a bar seems far less awkward than a solo guy randomly chatting with a woman or group of women. Again, it’s all about the execution.
Bad: “Hey. What’s your name? My friend thinks you’re cute” (Yes, I’ve seen this happen.)
Good: “Hey, can you settle a bet between my friend and I on what’s the best Tom Hanks movie? I say Big. He says Forrest Gump. What’s your favorite?”
Am I suggesting you and your wingman have a line ready? You bet I am. Some things are universal. Everyone has a favorite Tom Hanks movie. Everyone. Most people feel very strongly about it.
Will a good number of women see through it? Possibly. But, it’s creative and that might earn you points.
Choose your wingman wisely, though. Last thing you want is your buddy telling some nice lady how you wet the bed when you guys had a sleepover the first time you watched Big when you were 10.
Know when to fold ‘em
One of the blunders I saw Mr. Flaming Plane Crash make was that he lingered way too long. This woman was enjoying some time with a friend and he took up 20 minutes. That’s disrespectful. He paid no attention to the fact that she was physically turning back to her friend several times.
If you attempt conversation, look for clues of interest. Does she turn toward you or look round the room? Does she make eye contact or does she pick up her phone to look busy?
I mentioned to a man that commented on my previous article that the fateful conversation would have gone much differently if he just walked up, waited for a minute, and said, “Hi there. I see you’re enjoying lunch with a friend so I don’t want to take up your time. But you seem (insert any adjective that does not focus solely on her being hot) and I wanted to pass on my number if you’re available to chat sometime. You ladies enjoy your time!”
You can linger a second to see if she reacts but exit quickly. If she’s interested, she’ll call. If she’s really interested, she’ll engage right away. If she’s not interested, she’ll appreciate that you left graciously and you’ll never have someone write an article about you on Medium. I hear that happens…
Recognize your environment
Environment provides context. There are places where women will feel more open to talking to a stranger of the opposite sex than others. A book store is a place where you can naturally find yourself in the same aisle as someone with similar interests.
If you see a woman perusing a stack of Malcolm Gladwell books, you have an opener and someone who may very well be willing to give you a recommendation on what book to start with.
If you just said to yourself, “I never go to book stores” or “I have no idea who Malcolm Gladwell is,” just stop. Go to a bookstore. When you’re there, buy a book. Then read it.
Become a more interesting version of yourself. That is what happens when you read a book. The more interesting you are, the more attractive you are.
I’ll get off my soapbox now.
Some places may be seen as inconvenient or inappropriate. A doctor’s office. The gym. Divorce court. That last one really happened to a friend of mine. Also, don’t approach a solo woman in a place where she may feel vulnerable like a hiking trail or a running path. That’s a great way to get pepper-sprayed.
Of bars and beers
There are a few things that need to be mentioned regarding approaching women in bars. First and foremost, a woman sitting at a bar is not asking to be hit on. Sometimes, we just want an adult beverage. We should not have to choose where we sit in an establishment because every man thinks we’re free game. Remember everything I said about reading the room and looking for cues.
Second, don’t offer to buy a woman a drink. Contrary to popular belief, that is not why we’re at a bar.
If a woman you just met is expecting you to buy her a drink because you acknowledged her existence, that’s a red flag.
Most women don’t trust drinks from strangers. Alcohol lowers inhibitions and so offering more of that gives women the idea that they have an ulterior motive. Save buying her a drink for if you actually land a date.
Final thoughts
I know all of this stinks. We all wish it could be easier. It’s just not. I’m sorry that imbecile men have sold you a bad bill of goods with pickup artist strategies.
More than anything, I want to reassure you that your success in approaching a woman is not based on being 6'3" with huge biceps and all of your hair. We notice when a kind, charismatic, funny, respectful guy with confidence respectfully starts a conversation with us, especially when we don’t expect it.
Move outside of the realm of what a stereotypical dude would do and consider what a woman really wants. The only way to know that is to listen to them. Walk a mile in their shoes. It’s wholehearted and it goes a long way.
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